Just another recommendation for Keno Tractors. I bought a Jinma 454 with Loader and backhoe. Plus I bought the Yuchai Dozer all of it fall to winter of last year.
As Bob stated the 3 point on the Dozer is nice, I have some parts of my property so steep with no turn around that I don't like to use the tractor. I will drag the brush mower behind the dozer and can work the area that way. I probably invested alot into equipment (maybe too much) and think the others advice on a lot of track building can be done for 20k without buying equipment. Plus they are faster with the really heavy equipment and with knowledge of their operators.
Even after I paid to have 2 acres of brush, small trees and 10 ft tall blackberries cleared by a local exacavating company with a 140hp dozer with grinder attachment (they cleared it in 8 hours, at about $1300 cost) I still need to maintain it, hence the purchase of equipment. In addition I planned on carving out a lot of terraces and building a house, doing the excavation and grading myself so buying makes sense at some point.
Unfortunately I was like you, I didn't grow up on a farm, and I don't operate heavy equipment for a living. Luckily my father did operate heavy equipment for a career, and grew up on a farm. I recommend finding a local experienced operator if you don't take the courses as per others recommendations. Follow their advice on how to approach a project. It might save your life or equipment or both. Otherwise it's kind of fun to play on the "toys."