I LOVE your rationale shooterdon!! It makes complete and utter sense!
OK, here is the other side.... It also makes sense to do it this way.....
You could just buy an older tractor like shooterDon did. Something old enough to be affordable made of good standard parts like a reliable engine, simple hydraulics, simple electrics, no computer, and a basic gear transmission. Decide that y]ou are going to teach yourself about mechanical things by using the tractor as your teacher. The trick to what I'm about to propose is to start with the right machine. You want one that is basically running and from one of the brands with good availability for parts and workshop manuals. It sure helps to get a brand that has owners that like them enough to work on them. Try to save 10/20% of your budget for parts, tools, and workshop manuals.
All the simple tractors that have a lot in common with one another. You'll find that they are mostly 15 years old or older and from an era when tractors were built to be repaired by owners and therefore last forever. Common "cult" brands that have clubbish type of owners who do this are JD, Yanmar, Massey, and some older Kubotas. There are others. It depends on the area. I know one large farming area in my state where the "go to" used tractors are old Zetors. That's because there's a good dealer who has been there years and provides parts and technical help.
Frankly that Branson would have fit the bill perfectly, but having been in a flood is just starting from way too far down. Your money will buy a better machine that is just worn and beat up instead of terminally flooded. You can find decent older tractors if you read between the lines on tractordata.com & tractorhouse.com
Expect that it will have neglected maintenance which means it is going to need repair work in the first few years. Then use that as your motivation to learn how to do that necessary mechanical work, because learning about mechanical things and how to fix and build them is going to be a pain, but one that will ultimately pay you back many many times over your lifetime. Being simple, rugged, slow, and forgiving, a tractor is great for teaching you all these things. And by learning mechanics, that tractor will have made you instead of costing you money. Only real downside for a young guy is to accept that the tradeoff is the time you spend learning. So share that time with your kid. They love to learn.
All this can work for you because it did for me. It's more about lifestyle than about tractors. For this poor southern boy, learning how to" fix it myself f" was the key to everything good.
From there a person can get fix lots of other things too. Like building a house, getting free of car payments, maybe even finish HS and on to college....., he can do all of those things. I know because I did. And maybe even teach his kids how to do them as well.
rScotty