I know pretty much nothing about tractors but bought my first one 2 months ago. I wanted something for bush hogging the fields, tilling, digging post holes, towing stuff around, plowing/moving snow, moving dirt, rocks, manure, etc.. We've got what I guess you'd call a 'hobby farm' with right at 10 acres of fields and woods with a big garden and we keep 3-4 dozen laying hens and raise meat rabbits. We sell extra eggs and vegetables and some rabbits. Our plan for the near future is to expand the garden and get into raising some mini meat animals, cows and pigs, for personal use and to sell.
I checked around locally at was available, looking for what I felt was the best value for a tractor that would work for us and that we wouldn't grow out of. After a lot of reading and calling and checking with the dealers in the area we ended up buying a new John Deere 1025R, it's one of their 'subcompact' models. They had great financing, 84mos 0%, no down payment, a 2 year 'bumper to bumper' warranty and 6 year drive train warranty and we bought the extended warranty option which makes 4 years and adds transportation for warranty issues. It has a 23.9hp 3cyl Yanmar diesel engine, rear and mid PTOs, 4wd, 3pt hitch, power steering, and a bunch of little amenities. We added a block heater (gets cold here in Maine), 53" bucket, 4" tiller, and 4" bush hog. The price was right at $22,000 OTD.
Though we've only had it a short time, we love it. All kinds of jobs that I would have to move by hand or in a little trailer behind the 4 wheeler are now handled with the bucket. A big mound of rocks, chunks of cement, and dirt that was next to my chicken yard and bugging me for the 9 years we've lived here but was too much to move by hand was made into short work using it as a bucket loader. Now that it's cleared and leveled I can put an out building there like I've been wanting. I used it to plow when we got a foot of snow a couple of weeks ago, it was fast and easy to use. When I was cleared an area of alders I filled the bucket with my chain saw, hand saw, jugs of gas and bar/chain oil, hooked the chipper to the back and hauled everything out to where I was working in one haul instead of multiple trips with the 4 wheeler. It will also replace the Swisher pull behind rough cut mower I've been using behind the 4 wheeler for a few years to mow the fields. And, I can't wait to till the garden with it and not have to get the tar beat out of me with my walk behind tiller.
It's very easy to use, JD must put a huge amount of time and effort into making these things approachable and user friendly with people like me (tractor neophytes) in mind. Getting the bucket and/or frame off is a piece of cake, so is hooking stuff up to the rear PTO/3pt hitch. So far it seems to be pretty bullet proof and really rugged.
Obviously, our needs are a little different but I know that you can get graders, rakes, and a ton of other attachments for these. Also, they just get bigger from the size I got if that one's too small for you. I looked at used tractors but with the 0% financing and warranties it didn't make sense for me to buy used in my price range.
Like I said, I don't know much of anything about tractors except the one I've got but that's my tractor story. Hope it helps.
I wouldn't have one just for that reason. 
