This is an excellent book that will educate you about trailers and hauling and help you make an informed decision:
The Complete Guide to Buying, Maintaining, and Servicing a Horse Trailer https://a.co/d/aQiLVQQ
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Ditto this.
Go with 4WD - if you ever park in a grass field or a muddy parking lot you’ll need it. 
One thing to note with 1/2 ton trucks is that you will need a weight-distribution hitch when towing over about 5k lbs. This is something that’s usually tucked away in the owner’s manual.
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These are great questions. My dad is handy and would be good to come with me and look at/drive trucks and help/teach me maintenance but as far as “advice” he’s about as helpful as a screen door on a submarine. His advice thus far has been relegated to “Gas and an F150 or F250”.
Right now, I’m trying to figure out what my budget should be. As I mentioned, purchasing a truck/trailer is an “in a year or two” thing so trying to give myself some time to educate myself.
That said, definitely not my daily driver or only vehicle and I won’t really need room for folks. Let’s assume parking’s not a problem.
OK since you said talk to you like you’re five. I am writing this without reading other replies, so sorry if it’s repetitive. Here are your main choices:
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Truck: new or used. New = expensive; used = uncertainty about truck’s condition
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Truck: gas or diesel.
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Truck: brand. IMO not too important.
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Truck: half ton or bigger. You should really be thinking about the worse case scenario IMO, not just that you’ll always be hauling on flat highways with good visibility, no wind, and no idiot drivers around. And you’ll never haul somewhere where you’ll have to park where it’s wet. See my story below.
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Trailer: new or used
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Trailer: ramp or step up
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Trailer: BP (bumper pull, or towalong) or GN (gooseneck)
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Trailer: slant load or straight load
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Trailer: aluminum or steel
My story, which I have shared on another forum but not here.
Way back in the day before I knew anything about anything, I was getting my Pony moved from where I bought him to his new home. It was a 40 minute drive on an easy highway. He weighs maybe 600-700 pounds and would be the only horse in a small straight-load aluminum trailer. The only hiccup was there was a short steep driveway to get him out of where he lived. The barn owner at the new place came with a half ton truck for that trailer and was confident she could get him out.
Well, guess what, they tried multiple times to get him up that driveway and couldn’t. They ended up sliding backwards, hitting a tree, and trapping him in the trailer. He was trapped in there for hours while they tried to find someone with a real truck who could pull them out. Do you want that happening to your horse?
So when it was time for me to buy my truck and trailer, I got a 3/4 ton truck. I have never regretted it, even though it gets poor gas mileage. For a while, I was having connectivity issues and the trailer brakes off and on didn’t work. I got it fixed, but the mechanic told me that I didn’t need to panic about it because my truck was perfectly capable of handling that trailer without brakes. So what would you do if something happened to your rig while you were out, say the brakes went out. Would you haul your horses back with no trailer brakes and a truck that’s not designed for that?
I just wouldn’t want to haul with less than a 3/4 ton truck, OR a half ton truck that has a really solid towing package and is rated to tow at least 10k pounds. Such trucks do exist, I’ve been told, but I don’t know that they’d be much different in price and gas mileage than a 3/4 ton truck.
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and add a winch, we have a 12,000 pound winch on the front of our four wheel drive that has been used to pull others out
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4WD Yes. I can’t count the number of stuck trailers at horse shows I have seen. That ‘flat’ grass parking lot suddenly isn’t flat after that afternoon thunderstorm.
As for gas versus diesel. I hate saying it, but unless you can find a pre DEF diesel. Do NOT get a diesel. You don’t need it. I love diesels…but DEF has destroyed them unless you have to have the pulling ability and very few people actually do.
What you do need is a really, really solid transmission. Look for models that don’t have a reputation for blowing their transmissions.
On your dad’s advice, F250 yes. I hate Fords, but yes. F150 really not heavy enough. In particular when towing you are looking for weight and pulling ability that is low the ground. One of the problems with so many modern trucks is they are getting taller and heavier, but all that weight is up high and useless for pulling.
Our best, best truck for hauling horses was a 1993, gas, Chevrolet Silverado 2500 V8 4WD with an 8 foot bed and an Allison transmission. It was long and low (so very stable), with a huge engine and an transmission designed to pull. If I could rebuild its frame, I would. Rust has killed it.
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What endlessclimb said. You don’t need a diesel. And DEF is a bit of a pain.
I live in the serious mountains. I dont really need a diesel. I have one because of the environment I lived in when I first bought it, which was much more rugged than where I am now. I regularly contemplate trading it in nowadays for a gas truck, but haven’t got round to it.
I have a 2016 Nissan Titan with a Cummins diesel engine. They don’t make them any more. It is heavier duty than most 1500s but not as heavy duty as a 2500. If I were to replace it I would probably buy a gas 1500. The modern ones have a lot more oomph than they did.
A bumper pull will do you fine for local tooling around. I do the occasional long journey (9 hours each way) and we survive. Most of my things are within a couple of hours.
I have a Trail-et 2 horse straight load bumper pull with a dressing room. Its older but has always been well cared for. It is spacious and horse friendly.
I can tow one or two horses very easily with this setup. Its easy to park, easy to maintain, easy to hitch.
I feel safe in this set-up. I occasionally contemplate going for an SUV and a euro trailer, but haven’t done so, as we quote like having the truck around for other things.
People make comments like this a lot. Don’t fall for it.
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You don’t think a diesel is a requirement for steep grades and going up and down mountains? I only reason for diesel vs gas in my area due to short merges, having to get up and down some serious grades/mountains, and dual wheels for stability on the nail biter roads. My BMW has no issues but my Camry struggles on many of the roads. I don’t even bother with my Civic on some roads it just can’t without serious strain to the transmission. I test drove a F150 that did ok but I couldn’t imagine pulling a trailer with it.
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I’m not talking about hauling with an SUV or sport truck. I’m just saying that they might be able to make a gas 1500 work with a bumper pull smaller trailer IF they aren’t regularly doing 65 on a highway or hauling over mountains.
Personally… my experience is that I prefer not to haul with anything smaller than a 2500 / 250. And I am a diesel fan. I’ve had to push with a gas truck when on a major highway doing 70 fully loaded, and while going up a mountain, and even though I theoretically had plenty of excess towing capacity… it sure didn’t feel like that. It felt underpowered. With the diesel version of the same truck? I do not have that problem at all.
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Your short merges need horsepower, not torque. The grades benefit from the additional torque. Gassers make plenty of power/torque for 99.9% of your average horse owner’s hauling needs. They also come with DRW.
I have a 2 horse gooseneck that clocks in dry at 6klb, and diesel that produces over 1000 ftlb of torque. It’s overkill. I could easily pull this trailer anywhere with a gasser.
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My advice to first timers is always buy the heaviest duty truck you can afford then buy a trailer it can tow comfortably.
More specifically - agree with others to get a gas vehicle. You don’t need diesel torque for two horses and cost of fuel and def issues are significant drawbacks. 4WD absolutely. Don’t get too hung up on brand for your first truck. The family business has purchased many trucks and all brands/models have “Monday” trucks and real troopers. Having recently done exhaustive research on SUVs with a family member looking to downsize from a full ton diesel crew cab long bed, I would say look for a truck. Towing capacity of SUVs varies widely depending on the options and dealers are clueless about towing. When you find a capable SUV it will be very expensive. Family member finally bought a 3/4 ton gas short bed with very nice options for less than the mid-trim SUV.
A smaller trailer is less expensive and easier to drive. Obviously you want it big enough for your horse to be comfortable, but a 16h probably doesn’t need extra high wide or long. If you think you can make do without a tack room, skip it. A bumper pull is easier for a first timer/ occasional user to drive. You can always upgrade later! Be sure to check that weight ratings of truck, hitch components and trailer are all compatible.
Get truck and trailer vetted! Like with a horse, if it’s fine it may seem like a waste of money. But if something serious turns up it will save you money. Practice driving your new rig! Take it to a parking lot, back up, turn tight, slam on the brakes. Get your dad to drive while you ride in the trailer. Time well spent.
It is great having your own transport. Good luck and have fun!
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Make sure your dad likes you though. 
Agreed that having your own transport is the best!!
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Since you’re in the Midwest give “plow” trucks extra scrutiny. There will be a lot more wear and tear on the front end/steering parts, and of course more snow/salt exposure. Look for plow mounts up front - I circled them in yellow in the example picture below. They sometimes remove them, so also check to see if the lower bumper trim has notches.
If your dad has thrown out a preference for a Ford F150 or F250, you can poke around on the Ford forums as well as peruse Wikipedia for the various Ford engines and transmissions for each model/generation and then look for any recommendations or major watch-outs.
Also just in case for reference a 1/2 ton truck is the F-150 (or 1500 in GM/Ram) and for a 3/4 ton truck that’s the F-250 (or 2500 in GM/Ram) and 1 ton is F-350/3500. (The use of 1/2 ton, 3/4 ton, and 1 ton is a throwback to when that was the truck’s payload capacity of each level, but modern trucks exceed this.)
If you’re not concerned about it being a daily driver or having passengers, you might be able to find a good deal on a single/regular cab bare bones type fleet truck (it will be white ).
It won’t have the bells/whistles/creature comforts, but because it won’t have all that extra weight from the fancy trim packages it will also have a higher towing capacity.
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ok 5 year old if you buy an older diesel one thing your dad should do first is replace the vacuum pump.
We had a vacuum pump failure while exiting the interstate returning from a horse show with two horses, the brake boost was not there, if the exit ramp had not been very long we would have surely run through the intersection
Pump cost for the 7.3L Powerstroke was $35, it sets in front on top of the engine takes about 15 Minutes to change
The bad thing was truck had just had a “complete brake job done” two weeks before the failure of the pump. I went back to the shop to tell them for diesels a complete brake job they should in future include replacing the vacuum pump.
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Actually on the highway is among the easiest hauling I do (though the speed limit with a trailer, I note, is typically 55mph 
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I have also experienced the surprise of some mighty steep driveways into/out of horse facilities.
It’s worth thinking a bit about the kinds of places you will park and arrive at. I have a 108" width straight load trailer 2 horse gooseneck which is the max legal width. When I bought it, I was hauling large horses and often in relatively urban and developed environments.
I have no regrets BUT after moving, one of the places I used it regularly was a rural private driveway while my daughter was in 4H. Getting that sucker in and out of there was a !#$%# because of an irrigation fitting right near where the driveway met the road, and the turn and width was a big deal. Always worked, but if I had been buying for the smaller horses I had then and that kind of access, I might have picked something else.
When you are buying a trailer, note that it’s not like a car where you can just expect what you want will be something you can find, even new. There’s just not that level of inventory, and there may not be a dealer terribly near. You may be looking for a while or you might have to order one. What you can live with and what you’d ideally pick if you order might be a bit different.
I like having the tack room door on the driver’s side (so I can park the rig completely flush on the right if I have to). I like my tack room and indeed I keep most of my stuff there all the time, which saves a ton of time loading and unloading to go somewhere. I like ramps, I think they’re more versatile for other loads and for slippery conditions. If you’re driving to trailheads, or on narrower roads, a smaller trailer without a ramp might be better for tricky access points.
If you ever might need to load or unload or park after dark, lighting is SUPER helpful. It can be added aftermarket however.
I like at least two tie points on each side. You don’t know if you’ll be able to access both sides when you park, your horses might not get along or they might really need to see each other. The most convenient case is to tie on the same side as the tack room door. Again this can be added aftermarket if needed.
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I feel like COTH does overkill on the trailer thing. I started with an F150 and and all steel extra high extra wide 2 horse trailer. Towed that same trailer with a Grand Wagoneer. Got an extended cab short bed 1500. Moved to a 2 horse Trail-et- dressing room, extra tall, standard width, aluminum skin, steel frame. I live in SE PA. I have hauled 2 horses including a 2000 pound draft and a yearling appy/TB. I hauled to OH, MA, WV with some version of those set-ups. The trip back from NY was 1 horse but lake effect snow squalls. I never had equalizer bars. A friend’s SUV Suburban died. She normally used equalizer bars. I used her trailer but not the equalizer bars to pick her stallion up at Dressage at Devon with my F150. She was surprised she could not feel him move.
Yes currently I have a diesel F350 with DEF because that was what was available used. I have a 2+1 with Dressing room with a GVW of 12,000.
Another option depending on your state laws is diesel that has been tuned/deleted to by-pass the need for DEF. My prior F350 had this done by the prior owner.
All of my trucks have been 4 wheel drive due to mud/snow in my area.
I towed extensively with my F150/1500s. Multiple times a week, long distances, high speed highways, mountains and never felt unsafe.
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Totally agree. I think the problem is 1/2 ton trucks (and SUVs) come in so many different configurations. An entry model 150/1500 with the smallest engine, low axle ratio, no tow package looks the same from the outside as a beefed up one. The former might only be able to safely tow 4,000 pounds, while the latter can have nearly as much or more towing capacity than the smallest 3/4 ton models. But I think a lot of people either don’t realize that or had a bad experience with an ill-equipped truck and lump all the 1/2 tons into the same category.
I actually feel safer stepped down to a newer Ram 1500 from my older GMC 2500. The better technology means I feel like I have more power and stability.
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I’m glad you all said this - I have always been hesitant to admit that for years I towed my 2 horse steel slant with dressing room BP with a 2005 Dodge Ram 1500. The qualifiers are that it had the 5.7 HEMI (the same engines used on their HDs at the time), the right gear ratio, and I used an aftermarket weight distribution hitch (as required per the manufacturer). I never had any issues with feeling unsafe (like the tail was wagging the dog) and I still tow the same trailer with a 2020 GMC 3500 Duramax so I know both ends of the spectrum.
Back in the day the tow ratings for trucks was VERY subjective and each manufacturer had their own secret sauce as to how they came up with their numbers. Then the SAE J2807 standard came out. While it’s not perfect, it at least gives you a common way to compare tow ratings on trucks built after 2015 (when the Big 3 all finally adopted the standard).
I would venture that a lot of 3/4 ton trucks from the late 90s/early aughts could be rated lower than a modern 1/2 ton using that standard depending on engine/gear ratio/axles/etc.
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Oooooh. I didn’t realize there was no standard prior to 2015… which makes a lot of sense why “old heads” are so adamant about never trusting the numbers. I didn’t know they weren’t always published like they are published today. Now you can see all the specs (engine size, wheelbase, axle ratio, transmission, etc) for yourself and decide if it’s a suitable vehicle even if you don’t trust the manufacturer’s maximum capacity.
I had a 1995 GMC 2500 and IIRC it was only rated for around 10,000lb (I’m pretty sure it said it on the sticker inside the door). New 1500 models can be rated for 12,000+ if properly equipped. So I definitely agree with your statement that older 3/4 tons can be rated lower.
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