First off, WELCOME!
I've been operating tractors on-and-off for 30 years and just recently got a large enough property to "justify" a tractor.
No two people are exactly the same nor will they value the same features but I offer some things that I have been thinking about when it comes to getting a tractor - currently have a Kubota B2410 (24hp) HST and need to go BIGGER for field work.
HST is nice, for lawn work and extensive loader work, basically any time you need to change directions often or carefully control ground speed changes while at full power. This is often the case for me while tilling the 1/2ac garden, mowing, picking up leaves with the vac and such. One thing I do not like is HST is either "full blast" or sitting still for long periods because you just cannot hold a steady speed, "cruise control" is a farce (at lest on our B2410).
One thing to consider is with an HST you lose more HP thru the trans than with a gear transmission. Therefore, a tractor with lower name-plate rating but a gear trans will generally perform as well as a higher rated HST model. You also don't have to worry about thick hydraulic fluid in the COLD weather or pre-warming it for properoperation with a gear transmission.
If you ever plan to do field work, I would take an HST off the list of possibilities. Modern "shuttle" type gear transmissions allow rapid direction changes and even range shifting in some cases without comming to a full stop.
I prefer a loader for deep snow, there is a LOT less to go wrong with a loader than with a blower and you can use a loader all year.
Pulling posts takes more force than one might think. You can look up the 3pt ratings for my 2410 but one would think it would pull the post right out in east Tx sandy clay, NOT. I would look for a minimum of 2,000# at the 3pt for reliable post pulling and closer to 3,000 if it's something you have to do a lot.
Filled tires, YES yes and yes. Helps with leaks, you find the bigger ones quickly and can even prevent smaller nusience ones. Also makes the tractor a lot more stable by lowering the center of mass.
As to brand, the Jd WILL hold it's value better than anything else in the CUT and larger models but that's not to discount Kubota and the like (NH, Case) because they will perform very well too. THE one overriding thing I like best about JD is that they offer FACTORY attachments and impliments for almost every tractor they have ever sold. You can got to the dealer or on-line and see what is available for your tractor model and no other manufacturer can even come close to JD in the sheer number of attachments that are tested and verified to work with your machine. In my book, that's worth a lot.
