Why not focus on yearlings? Either board it at the breeders or stick it in one of the local fields you mentioned. You can work with it doing the basics, then when it’s time for your gelding to retire - they can switch spots.
Come shop in the midwest. $10k can find your a very nice horse out here.
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Buy a yearling, board him at the inexpensive place while he’s growing up. In 3-4 years, cycle the older guy down to the retirement board and bring the young guy into training board.
StG
You will get no flak from me about not wanting an OTTB. Despite their many proponents, and there are nice horses among them, my general feeling is “Why would I want to buy something that is purposely bred to run really fast by the time it is three years old, when that in no way resembles the job I want it to do?” How is the average person supposed to pick out “the one” that will last 20+ years?
I have an almost-30 year old Irish horse. Back when I was shopping, every single one I really liked was Irish. He was a rare find and should have cost more than he did, and even so was a stretch. This time around the horses I really like are still Irish, but shorter. 
And while I could now afford to pay what they cost at 8-9 going well under saddle, philosophically I am just NOT going to write that kind of check for a horse. So a couple of years ago I bought a yearling Connemara pony and he is parked in a field with a small herd and a knowledgeable barn owner whose job is “keep him alive and in one piece until he’s three.” Which is… next spring!
For the record, this is not that much cheaper… it’s just spread out, and I get to enjoy more of the growing up process. (Or, I would have, if we were not dealing with this plague.)
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The best horse I had was a Trakehner that was being sold for $500 back board. She was the perfect horse for me.
StG
Not trying to talk you into a TB if you’re dead set against, BUT…
If you live near a TB breeding or racing area, you may be able to get a 2 or 3 year old with much fewer miles. They often give away or sell for super cheap the ones that just aren’t going to be fast enough. They have usually trained for a year or two, maybe run once or twice. They’re to slow to really hurt themselves and usually have really great temperaments.
I need one of those for my 4 year old!
we have two of each, two white little things and twin grand kids
the twins took them to Bonnie’s 21st birthday party for treats
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Two words: pony cross
I have a 15hh New Forest Pony x TB and he is everything you’re looking for. Fantastic gaits, an absolute dream to ride and just a really cool horse to handle. Super smart, spectacular ground manners and very low maintenance.
Picked him up for $1000 out of a field advertised as a somewhat difficult project horse that needed a restart. Think pony brain but with thoroughbred sensitivity. He absolutely did need a lot of work: vet, massage, correct farrier work, plenty of tack tweaking and a very patient/finessed riding and handling program.
Totally recognize that my situation is unique, but I think you absolutely could find something similar in your price range that isn’t quite as big of a project but still that type of ride you’re looking for.
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Now this is just adorable clanter! Too cute!
My vet would kill me 
he specifically told me NOT to buy any of those tiny devil horses for my kid. I think he sees a lot of ill-behaved and poorly trained miniatures, poor guy.
Snort. Well I’d like to know where you are finding this is affordable retirement board with good care. I can find two things: High end facility at 1000+, or back-yard with some combination of questionable fencing, no ring or crappy turnout, 500. There’s not much in between.
There are a number of small-time warmblood breeders in MA. I don’t know any of them personally, but I know of a couple with small farms. They usually breed for dressage or are dressage people, and the foals are often sold pretty quickly. It’s more likely to get a deal on one if it’s 6 months old and still hasn’t sold.
Honestly it sounds like leasing might be a better option if you want to compete in H/J. There are a lot of people that care about their horses and what happens to them, and would be happy to free lease the horse, particularly if it needed a little maintenance or if it was a little quirky, to someone who also gives a crap. It’s not always about the lease fee. I would have thought you’d be able to fall into one of those situations at your own barn, but a lot of that depends on the culture at the barn and what the trainer is like. If the competing isn’t as important, given the other things you’ve mentioned- a trail ride, some dressage, some jumping- you might want to look for an event horse. They are generally well versed in all, and much more affordable than h/j horses. A lot of the types that have been mentioned in other posts are things that would consider nice all-around event types. I guess it will really depend on what your goals are, or what you find, when you are ready. Also, the horse market in New England is an absolute cluster F right now so don’t base your decisions on that (not sure if you are native or not). I know of several people that have been looking and it’s like a hot real estate market- things are sold same day as they get posted to the first person who looks at it. And no one went to college this year so there is a serious lack of “free lease, off to college” types as well.
I have an “in” with some people locally. Literally nothing confirmed, however the barn owner where I’m at knows a lot of horse people in the area who have a few horses at home. They’re people who are well off, have land, are older, and have had horses most of their life and now just enjoy them in their backyard. This type of situation has been mentioned off handedly in conversations with BO- obviously a real conversation would have to be had prior to deciding to retire him and purchase a youngster. At this point I’m purely in the coming up with ideas and putting out feelers phase!
Thank you all so much for your input! Lots to think about.
Think outside the box. IF you think you have the time, purchase a proven broodmare and start babydaddy shopping instead of budget-half-finished horse shopping. (“Proven” meaning she is in decent health, has two digits in her age but not too far along in that range, has had previous foals.) A plus would be if she’s rideable. You can choose a performance stud of whatever breed for a budget friendly experience. AND you get to raise the foal with all the benefits that brings - which you already know is wonderful, from your post. Personally I would buy a draft or draft cross mare and breed to a lighter warmblood or a TB with a calm, trainable willing temperament whose athletics are confirmed in jumping and dressage rather than racing, but that’s just me (yes, I have known some racing stallions with lovely temperaments who went on to dressage careers so please no one get their breeches in a twist I am not dumping on racehorses). As an investment I might suggest this: get your baby and then breed your mare again with an idea of marketing the resulting foal as a young horse or green under saddle - draft crosses are getting really hard to come by as people love the calm temperaments of the drafties coupled with the athletic abilities of tb’s, Morgans, Arabians or whatever you want to outcross to. Just a thought.
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our farrier, bless his heart, jokes that he gets to lay down on the job… the smaller white things stands 26 inches
they are all well behaved, otherwise they would have been sold
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Babies are only cheap(ish) if nothing AT ALL goes wrong. And you have a place to raise it with age mates. And the. You still have an animal to feed, shoe, etc for 4 years before you can ride it.
If it’s an NI foal, you loose the mare, etc, etc, it can quickly eat up your original budget and any extra you may have.
My my my. WHAT a ray of sunshine! It was only a suggestion, and one that worked for me quite well. I am not suggesting doing it on the cheap but within a forecasted budget. Far cry from being “cheapish.” The OP enjoys working with young horses. This is just another suggested pathway. I pity you with your outlook you won’t experience the joys of raising a young horse because of what “might” happen.
OP asked about inexpensive ways to source nice horses. I don’t think there is anything inexpensive about raising babies. You take the ‘normal’ horse risks and multiply them by two. And then you still have years of feeding a horse you can’t ride.
As someone who also has to do things on a budget and also doesn’t have a lot of land, I’ve thought all of this through from my personal perspective. It doesn’t make sense to me financially. I’m not sad at all about ‘missing’ the experience. I’ve worked with tons of foals and don’t really enjoy it. I’d take a three or four year old ready to get going over that any day.
We don’t have to agree on that. I rely on people like you, who do enjoy foals, to raise the young horses I prefer.
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