I was in exactly the situation you are now 14 years ago. There’s very few places on my property where it wouldn’t be easy to roll a tractor. A sub compact tractor is going to be more stable than a compact on the side of a hill. There’s all kinds of places I can go with my lawn tractor where my compact tractor would roll over. There’s nowhere that I can’t go with my zero turn mower, which has a very low center of gravity and a steering wheel so it sticks to very steep slopes. If I had a $30k budget and your property, I’d rather have a $20k tractor and a $10k Cub Cadet ZTR (which is what I use to keep up with 52+ acres) I mow with the mower, the tractor is for bush hogging, fixing the driveway, etc. A larger, more expensive tractor wouldn’t do anything that I can’t already do. I’m maintaining a nice looking property, I’m not logging, digging giant holes, etc. The ZTR will mow the roughest pasture imaginable as long as I don’t let it go completely, and if I do then I can bush hog it.