I have 40 acres, (hence my name), of which about 20 are fields, mowed with the rotary cutter (bushhog). I have several swampy (boggy to y'all up north, I reckon) areas. My tractor is light enough with the wide R4 tires and 4WD to move across the muck without sinking, but heavy enough to load the FEL with dirt and haul it around. I also have a two+ acre pond that needs spillway maintenance. My 3 acres of lawn, plus 3.5 miles of walking trails are maintained with the finishing mower. I do more wrenching on the attachments than on the tractor. I use the FEL constantly. I don't own a phd, but borrowed one on two occasions to put up the fence posts. Snow is only a rumor in these parts.
Here's some of my experiences. Perhaps you'll find useful info...
Bought a used Ford 4000 (20+ years) to start with. Worked pretty good for two years, except the skinny R1 ag tires with 2WD would break throug the crust on the swamp and bury the tractor right quick. Then it started having little problems. I'd spend two hours fixing the tractor before I could use it at least once a week. Mostly minor repairs, but aggravating, especially when I had to spend the day going to buy a new part and installing it. When I got the okay from the CFO, I went shopping. I started with a basic price range, ($18K) and then started looking at everything available for that price. I compared weights, horsepower, attachments, #of speeds (forward AND reverse) or other type of transmission (some don't really have specific gears [HST]). I got the Kubota, (about $21K) because I felt that it had the most horsepower for the money, but still was the right size for my needs. I've never wished I had a smaller tractor, but occasionally have desired a bigger one, (mostly when trying to move a lot of dirt).
Things I found I couldn't live without, but didn't know until I got the new tractor: 4 wheel drive (I highly recommend it), R4 tires (your needs may vary) rear hydraulic controls, power steering, comfortable seat.
As for attachments, I buy them as I can afford them, but mostly I buy with an eye to the future. I want stuff that will make my life easier when I'm old and feeble. The sickle bar mower was expensive, but I can cut along the edges of the pond with no trouble. Way better than a hand held gas trimmer. Along with attachments, I've had to add to my tool collection. I'm a tool fanatic, but here's two I use all the time: an impact wrench (mine's electric) and a torque wrench. They are easy to learn to use. Finishing mowers cut just like a lawn mower and eliminate an additional gas engine that must be maintained. However, the blades will need to be removed for sharpening. The FEL is great for lifting the mower to get at the bottom.
Safety: Since you say you are a tractor newbie, I highly recommend reading as much of the safety forum as you can. I learned a lot there. Don't let your tractor kill you. Plays **** on living your dream.
Good luck. The folks on this site are great. Don't hesitate to ask questions.