I’d board first to determine your priorities for building and see how your horse does in the different climate.
We get that nonsense type of temperature swing where I am too. Nobody runs out to change blankets. Dress them as right as possible once every 24 hours is the way I’ve always done it, and the way everyone (many of us self-care boarders) does it still. Perfect? No. Occasionally a horse will get too warm in spring or fall, but they don’t die. Occasionally horses will be a bit underdressed, but those tend to be days where they come in early, and nobody dies or suffers for long. Also, handling them daily, you get an idea of who ‘runs hot’ and can get away with lighter clothing on a cold day and who ‘runs cold’ and needs heavier clothing always.
Do you own a light spring jacket and a heavy winter coat and possibly something between the two? So do most horses who are expected to keep working all year round without overheating, keep skin conditions at bay, and stay at a reasonable temperature without shivering or eating their owners/barn owners out of house and home.
Editing, that it takes no more time to keep on top of blanketing than checking the weather app, talking to everyone else who is staring at their weather app and coming to some sort of consensus 
The actual blanket changes take no time because we’re going to take off/put on for grooming and working them anyway.
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I think this is a wise, compassionate, and selfless plan.
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I waited to reply until I was at a computer.
I grew up in WNY, mostly in the southtowns (snowbelt area) and we always had horses at home, my parents and later my dad, brother and I ran a boarding barn for many of those years.
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Snow - don’t panic about it, we are used to it a generally speaking the roads are well plowed and salted as needed. Make sure you have good tires and take time to learn how to drive in it. The BIG snow storms that drop several feet are rare, limited to a relatively narrow band, and usually forecasted several days in advance. If one hits then just stay home and wait it out, when things clear wait for the street crew to come through or pay someone with the big machinery to clear you out. Most of the time a regular snow blower or plow will be sufficient to keeps driveways clear.
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If you choose to buy a horse property be careful with zoning - most towns require at least 5 acres to keep one horse and an acre per additional horse up to 10 acres, then you can do what you want. Smaller farmettes like you see in the south and west (my mom had about 1.9 acres outside Denver zoned for 3 horses) are very uncommon in this area so figure that in when looking at property.
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For boarding, here is a place to start:
Erie County Horse Boarding and Farms | Facebook
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If you set up a farm, plan for snow - where to put it and getting between buildings when it is snowing, and plan for MUD. Make sure you look at the lay of the land and plan for drainage and how will it function during spring thaw/ mud season.
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Hay is grown locally and reasonably priced compared to much of the country. You can find nice timothy or mixed grass hay for $4-6 for a 40-50 lb. bale, alfalfa is not common in the area though it can be found.
Most of the rest has been covered.
I am surprised to hear your friend thinks boarding isn’t a great option. Yes, your options are more limited, but there absolutely are quality boarding options in Buffalo. It may just depend on what you’re looking for. For example, my one friend has her horse at a higher end show barn in a training program - probably not what you’re looking for. But my other has her older gelding at a lovely full-care facility where she takes weekly lessons. (Both in Buffalo).
I’m not sure what your budget for retirement is, but you could look into the Maddens in Cazenovia. They have quite a few retirees coming from warmer clients, and would be around 3 hours from Buffalo. Obviously I don’t know if your horse has any health concerns/conditions that make you more concerned about adjusting to the climate, but I promise it isn’t the artic circle up here and horses really do adjust quite well.
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And THIS is what makes you a wonderful horse owner, right here.
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An insulated barn is a luxury and something you won’t find in most places ( boarding or at home) . Now you will find the tack room & lounge area insulated and heated but that is it for most… even in MN.
Think about how you feel when you just stand in the cold. So much easier to get warm when you can actually move. Horses are no different. I have never put food and water out in th elements ( hot or cold weather) it is always in a sheltered place under the lean to off the barn.
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But they are not going to generate heat trying to get tiny amounts of hay out of a hay net/ netted bale/ feeder , which is what many seem to use. Maybe working to get that hay out will help them forget how cold they are 
My barn is not insulated, but it is built on an old bank barn foundation so 1 wall is 3’ in the ground. The roof does have thin, foil insulation under the steel and the walls are board and baton with house wrap underneath. With a few horses in there it is regularly 10-15 degrees warmer than outside in the winter, especially when mother nature adds a few inches of snow to the roof for added insulation.
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Not insulated by traditional standards no, but the bank wall and the little extras you added do make a difference for sure.
Even in an uninsulated barn with the windows open it is 5-10 degrees warmer. This has been true of every single barn I’ve been in over the winter, which is dozens. A truly insulated barn can be a solid 15 degrees warmer.
Perhaps your horses opt out of a hay buffet and go wander around to self warm but I’ve truly never seen it. When it is cold they hunker down behind a windbreak or they are eyeball deep in a roundtable, hay bag, or whatever they have to eat. There is no movement of note that would create any appreciable extra warmth. Even walking to and from the water trough isn’t generating the 5-10 degrees that a partially enclosed barn with a full wind block will provide.
I’m fully in favor of outdoor horses and think that for arthritic horses or mental well-being some should be out 95% of the time, but I just don’t think the warmer outdoors argument holds any logical foundation.
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Mine have never been visibly shivering/ cold but they do like the ample hay regardless…
I don’t believe that you really know what I understand. I was talking about a deliberate action, and digesting/processing the food that they are given is not a deliberate action by a horse.
Also, I thought it wasn’t necessary to mention things horses do that are commonly known, just one that I didn’t think many people realize, which is that moving around warms up horses. That concept seems to run counter to what I’ve seen a lot in people I’ve met in person, which is the idea that putting a horse in a stall in cold weather makes them completely warm. After all, it’s what we people do, go inside to warm up.
I only meant to say that shutting a horse in a stall restricts their ability to move around, and tried to explain how that relates to warmth. Maybe not so well.
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Just another piece of input: I lived in Rochester (not nearly as bad as Buffalo) and in Cleveland for most of my adult life. Re Buffalo - do some serious homework on the areas that get most affected by lake effect snow. Don’t buy there, lol. For example in Cleveland, the west side of the city was much less likely to get dumped on than the east side. Its my understanding that east and northeast of the city is better. South is tougher. Storms come across Lake Erie. The temperatures aren’t horrible as the lakes can moderate them a bit, but you will also see precious little sun…
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Ha ha! Yes about the Land of Cleve! I lived in Oberlin and rode at Chagrin for a while in the 1990s. Weather on one side had absolutely no bearing on the other!
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I understand the dilemma of what’s best for an old horse. Good luck to you during this challenging time. Take comfort in the fact that he is going to have a peaceful, warm retirement. The fact that he made it to 28 is a reflection of your dedication to him.
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not to get off topic, but I boarded at Chagrin Valley Hunt Club for a number of years (those were my hunter days). Roughly 1994 - 2002
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No. You said the coldest place for a horse is a stall. You also said the only way for a horse to warm itself is by running around.
Both statements are completely false. Please just stop. You’re only digging a deeper hole for yourself by attempting to backtrack with but, but, but.
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In a boarding barn of any size, if the horses are brought in and the barn can be closed up tight, it will be 10 to 20 degrees warmer in the barn. I’ve experienced this at numerous barns.
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Same experience. I’ve always kept a small digital thermometer to monitor temps/humidity. Even in the most primitive barn we were in and having the preference for ventilation in the winter, provided all the horses were in their stalls it would still be 10 degrees warmer even with it being a small, 7 stall barn, minimal insulation and not shuttering it up. And I was there for two rougher winters. Buckets would need ice broken through cold stints, but the horses never came close to freezing. And none of them were blanketed either for that matter. Inside or outside.
The better insulated barns stay closer to 15-20 degrees warmer than outdoor temps. My current barn is a much larger barn than the primitive barn, but with 5 horses and it still holds true. Unless we have a week in the 20’s, we hover well above freezing with no need for heated water buckets. I don’t think we even had buckets freeze this winter for a day. That barn also get regularly opened up in the winter and is well ventilated.
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