A JD 3032 with loader would be my vote for something that should last probably as long as he will be able to drive it without a lot of repair costs. I think the new ones now have a power train 5 year warrantee.
But that is about 15 grand if you find a dealer that has had one on the lot a while. Probably not within his budget.
My FIL bought a new JD 970 with loader and used some of his retirement funds to do so. This has been 10 or 15 years ago and he has enjoyed it immensely. He also thought he could not afford it, but after looking at 20 year old used stuff pretty beat up for almost as much money, he bit the bullet. He has had some repairs, some of which we have taken care of, but a lot of that was his lack of mechanical apptitude, a grandson driving it, and extremely poor eyesight. Had the tractor had an easier life I think the repairs would have been minimal.
If you can at all swing it John, get a 3032JD. That is almost identical to the 3038 you saw in my shed. They are price cometetive with most brands and parts or service if needed is available. You will not regret it every time you climb onto it.
