Just went through what you are with about the same budget. I was amazed at the prices of new tractors and good used ones. I first considered going w/ something new and getting a FEL later, but I have a dump truck and that seemed silly. Also, the new tractors seemed to have too many bells and whistles I didn't need or were very basic and over priced or were from overseas and of questionable reliability and quality (just my opinion - don't kill me!)
I went to all the local dealers and reasearched private deals as far as about 8 hrs away from my. I found a used Ford 1910 at a NH dealer right around the corner from me. It had turf tires, Dual loader (which looks light duty) and about 1500 hrs. She wasn't pretty, been store outside, but seemed like it would do everything I wanted. After alot of research, uncertainty, and advice from this list I put money on it. Later I found a leak underneath that both I and the salesman believed was a minor clamp that would be fixed. Turned out it was a seal in the transmission and the entire tractor had to be "split" for it to be repaired. Had I gotten this somewhere else I would be facing the repair bill plus getting it back and forth to the shop. Going with a dealer meant it was done without cost to me before it was delievered to my door. I've seen many posts here saying one of the most important purchase considerations is being comfortable with the dealer and now I absolutely agree.
BTW: 1910s are four wheel drive and @ 30 hp, which I've been advised is about minimum for "serious" brush hog work and the other things I wanted to do. I paid 12,800 for the tractor packaged with brand new Woods 72" finish mower and box blade, 60" brush hog, and 84" Land Pride rake.