Welcome to the forum, SW. You'll find a lot of support, knowledge and experience among the members here. You'll also find that most of us are eager to help you spend your money.
FWIW, here are some basic recommendations:
HP range- 20 to 30HP 30HP is normally enough to handle a 60" brush cutter. Next step down is 48" which is quite limiting if there's a lot to mow.
Transmission- HST simple, intuitive, easy to move tractor precisely, productive for loader work, most in this size range include a mid PTO that makes a mid mount mower possible in the future. Very convenient in tight spaces.
Size- Small CUT (Kubota B series) up to a small utility tractor (NH TC30) but larger than a SubCUT (BX series) The CUT will give you better ground clearance for that unlevel acreage that needs to be leveled and a full Cat I 3 pt. hitch. SubCUTs tend to hug the ground and their 3pt. hitches are of limited utility. A CUT will accept a wider range of 3 pt. implements; the small utility tractor will accept even more.
3 pt. hitch control- position control is superior to 'quarter inching' giving you an infinite number of repeatable postions against quarter inching's two repeatable positions (full up and full down)
Tires- Probably R1 Ag tires would give the best performance on most tasks. If a lawn is in the future, consider R4 industrial/ribbed tires. If you fill the tires with fluid, you'll get better traction and stability, but you'll also leave your mark on the landscape.
Make- The big three (New Holland, Kubota, John Deere) with the possible addition of Kioti. You don't want to tinker so choose a dealer nearby, one whose maint. shop has a good reputation. Remember, getting the tractor to and from the shop for work will be an issue. You might want to consider a trailer.
Front End Loader- get the strongest your tractor will handle. Bucket hooks are a necessity and the dealer will weld them on for you. A toothbar would come in handy if you expect to dig...you can add that later. Look carefully at the specs for the loaders you consider. Make sure you're comparing apples to apples. Some loaders are limited in lift height.
Specific recommendations (I'm most knowledgeable with Kubotas):
On the low end-
B7510 HSD (21HP); LA302 FEL lift height limited (<6ft.), quarter inching hitch control
mid-
B7610 (24HP); LA352 FEL lift height limited, quarter inching control
high end-
B7800 (30HP); LA402 FEL lift nearly 7ft., quarter inching
-
B3030 (30HP); LA403 FEL lift >7ft., position control hitch
- New Holland TC30HST (30HP); bigger, heavier & stronger than
B3030, position control
Many here will tell you a smaller machine will do the same work a larger tractor will do, it'll just take longer. This is true. It's also true that a smaller tractor will do some jobs the larger tractor is simply too big to do. But only you know how much time you have for tractor work. The larger machine might be needed to allow you to complete tasks within your time constraints. Usually you'll get more tractor per dollar spent with the larger machines. On the other hand, small tractor maneuverability is priceless when you need it.
Visit the dealers, talk to the sales people, make them aware of your needs and background and, above all, try out the tractors you're considering. See how they fit, feel and operate and make notes of your impressions, both good and bad...for both the tractor and the dealership.
Shopping for and choosing the right tractor may seem like a hassle now; but once it's over, you'll miss it and want to do it again. So enjoy it while you can.
Bob