In the 30 hp range you have 3 basic choices. Japanese, Chinese or Korean.
CHINESE: Jinma, Kama
JAPANESE: John Deere, New Holland, Case, Kubota, Massey
KOREAN: Mahindra, Kioti, Branson
Regarding Mahindra specifically, some of their tractors are Korean, some are Japanese, I believe the smaller sizes are Japanese Mistsubishi tractors, and at rougly 30hp on up (I may be wrong on the transition point) the Mahindras are Korean. By the way, Cub Cadets are the same, under 35hp they are Japanese, but 35, 40 and 45hp models are Korean.
UNDER 30hp you can take the list above, but move Mahindra to Japanese. Add Cub Cadet to Japanese.
The Chinese tractors have a reputation for low price and lower fit and finish, fewer features and more basic design, also for spotty dealer support. Generally these are very heavy machines and more like old ag tractors than modern cuts.
The Japanese tractors have a reputation for being the highest priced but with excellent fit and finish, excellent ergonomics, and a wide range of features from minimal to maximum depending on the model. Depending on the brand and model, they can be ultra light or modestly heavy machines (very few fall into the very heavy category).
The Korean tractors are rapidly gaining a reputation for excellent fit and finish, good to excellent ergonimics, and often a very good value for the money (although that seems to be regional and in some areas they are as high as the big 3 Japanese tractors). They are also very heavy tractors.
Now to start up the LIGHT versus HEAVY debate . . . with implements the tractor with a greater advantage all else being equal:
HEAVY ADVANTAGE (more traction)= box blade, grader blade, sub soiler
LIGHT ADVANTAGE (less compaction)= lawn mowing, tilling the garden
NO REAL ADVANTAGE = Post Hole Digger, Sprayer, Rotary Cutter
FEL work, this one is really open to some heated discussion, generally a heavier tractor will have more capacity than a lighter one, but that is not always true. When digging into a pile a heavy tractor has some advantage. Generally, however, every tractor, light or heavy, needs some serious counter balance to work a FEL safely. I would give a slight advantage for FEL work to a heavier tractor, but I would be more concerned about BALANCE. If the tractor is heavy but has more mass in front of the front axel than a mid-weight tractor, the mid-weight tractor might have better balance and acutally need less ballast to get the correct balance. So for FEL work, a simple LIGHT versus HEAVY arguement becomes harder to defend.
BigAl and I already hashed over the GEAR versus HYDRO debate a little bit. Hydro has added costs that might bust your budget, it also eliminates many different tractors from consideration because some brands simply don't offer Hydro. But it also has some serious advantages for some tasks. You have to decide if you can afford it.
What you really need to do, BEFORE you pick a brand or a size (hp) is to look at your tasks. Decide what tasks you will likely do for the most hours per year. I am not the only one who questioned the size of machine you are considering, but given your lot size, I have been the most vocal in saying that you are looking at too large of a tractor based on the tasks you listed. You still have to decide for yourself.
To analyse your needs, look at your work on your 5.5 acres as you listed them . . . For example, if you are going to mow the lawn 30 weeks a year, and if it takes 2 hours to mow the lawn, then a typicaly year will have 60 hours of lawn mowing. If you are going to grade the drive way and it is 400' long, you will likely do that 2 to 4 times a year, perhaps, 4 hours each time, so roughly 12 hours a year (combination of box blade, FEL work). Post hole digging takes about 1 minute per hole (actual drilling) so if you have to put in 2000' of fencing with posts every 8', you will drill 250 holes which is just over 3 hours (that does NOT include set up time for each hole!) but once that work is done, it is DONE for a decade or more. Rotary cutting may occur once a month for 3 or 4 months at 2 or 3 hours each time, so about 9 hours per year.
Once you figure all that out, and they will be rough guesses, then you can decide what type of machine is best for you. Then look at the brands that has those attributes. Ignore the sales pitches that "this is best" or "that is an advantage" and go with the facts for YOUR property. Eliminate any machine that does not have the features you need or is of the wrong type based on your situation.
ALSO, SteveM gave you some very good advice about dealers, I wish I would have said that!
