Often times a decent sales person at the dealership is a good resource. I was lucky to find them when I got mine. The trick is patience, you should visit at least four dealers, even if it means traveling a little to shop. Don't get me wrong, buy local if it makes sense, but shop around as well.
Tell them what you want to do with the tractor, then see what they recommend. Some will try to oversell, others will try to sell what's on the lot already.
We have about 10 acres, partly wooded, some flat, some hilly. Add 2 horses, plus barn, plus fences, mowing pastures, etc. We have a 5 foot Land Pride rotary cutter (bush hog by any other name), and mow the unused pastures twice a year, plus mow about 20 acres for a neighbour. It takes a little time, but it's amazing how big a dent a weekend puts in the mowing.
The 3400 or 4400 Kubota may be a good fit for you too, plus being cheaper. If you use square bales, moving round bales isn't an issue. Either will handle up to 1000 lbs on the loader, so ordinary round bales aren't the end of the world either.
By all means hire the heavy work out (stumps, big rocks) If the rock's the size of a house underground, put a flag next to it and mow around, seems like the easiest solution to me..
If you're comfortable driving a standard shift, gear tractors are fine. HST is convenient. Drive both before you buy, and see what you like.. I don't like HST, personally.
Loaded rear tires are a must for any serious loader work, you'll probably want R1 tires (agricultural style tread). 4wd is a real plus in mud, snow, or for loader work.
Cab is plus and minus.. plus comfort, minus when it comes to clearances, visibility, fogging, opening and closing doors, etc. Personal preference, really.
Someone mentioned bigger tractors mean bigger implements, and he's right. Wrestling even smaller sized implements, such as post hole diggers, rotary mowers, spring harrows, etc are gonna make a tough country girl out of you in no time, but that's a good thing...

And there are easier ways to hook up, they just take a little patience and some leverage (crowbar).
I sleep well at night after a day on the tractor cutting firewood, plowing snow, etc. I'm willing to bet the number of real farmers with insomnia can be counted on one hand.
Shop carefully, keep in mind what YOU want to do with it, and you'll be fine.
Chilly