So, not bashing any brand, but the budget you have will probably get a 25hp compact in JD or Kubota, with a cab and some starter impliments. That same $40k will fully equipped a 40ish hp TYM, LS, Kioti. It will also get a very nice MF1840M I think. Heck, I saw a local dealer selling a brand new (open station) MF 2860M power shuttle, with loader, for like $38,750. I would fully expect a cabbed MF2860M to be in the range of $55k, but the MF1840M cab should come in around $35k, and leave you 5k for impliments. That buys a Box Blade, Bush Hog, and Tiller, or more if you hunt used stuff.
Didn't catch your location, but I think you referenced UGA, so Georgia. Consider this, there is an absolute ton of used 6/7/8/9ft equipment through out the SE US, that is too small for 'farming' but to big for 'hobby' and you can get some screaming deals on a 3 bottom plow, or a 7/8ft disc. Sure, maybe it's a 4 hour drive to pick it up in Valdosta if your in Athens, but to save $1000 on a impliment....
Where I was trying to go with that; your not going to use a CK2620 or L2501, or TYM264 with a 6 or 7 ft disc. If you go to a DK or higher HP MF1840 or so class machine (TYM357), you open some older but actual agricultural tools to your inventory.
Another option, I haven't seen mentioned, if you really want to do pumpkins or whatever; a small cab machine for every day use; and something like a Ford 4000/MF165/265, or whatever for tillage work?
Edit: I'll add, I'm not really that familiar with the 1980s JDs/IH-Case stuff; came from a Ford/Massey area