I'm going to copy & amend (where needed) what I put on a similar thread recently as it's very applicable.
There's Lot of good advice so the only things I'll add are:
Consider the tasks you need/want to do and consider the time you'll have to do them (if you already haven't). There's a lot of tractor sizing advice out there, but so much of it focuses on the tractor rather than the user needs/tasks and the timeliness of completing said tasks. .....and as much focus is put on tractors they're really just tools (or more appropriately tool carriers) and they shouldn't drive the purchasing/sizing decisions themselves. It's that identifying of tasks and time allowable, along with any max/min constraints (e.g. loader lift capacity, max implement width to fit in/through tight spot) that tends to be much more helpful in determining the size of the implements/attachments you'll want/need to purchase which in turn drives the size & power of the tractor along with any additional options that would be helpful to add to the tractor upfront (e.g. rear remotes, top & tilt kits, 3rd function valves on the loader).
Something else that may be worth considering is how much driving around the property you'll be doing with this tractor; from what I've seen it's usually the case that the smaller the tractor the lower the top speed and at low at low speeds a few extra mph can make a difference (if it can be fully used).
While it's been a few years since I bought mine, I still recall that the "bang per buck" generally got better going larger as the price difference between sub-compacts and various sized compacts isn't all that great when considered over the life of any loan (and with the low/no interest rates ) -- or the expected life of the tractor. Granted going larger/heavier can also add transportation considerations (if moving the tractor to other properties is part of the task list).
Not trying to undo anything you've already researched or analyzed, just wanting to ensure that a few things that seem to frequently be overlooked aren't --- and even when everything seems to point that the tractors you're looking at are appropriately sized, it's probably still worth talking to the dealer(s) about how low hour trade-ins are handled if it turns out the initial tractor you go with doesn't quite fit your needs in practice (was actually a conversation topic my tractor dealer brought up with me when I bought my current tractor).
Now I'm going to disagree with Jeff slightly when it comes to mowing based on my own mowing experiences (which may not be entirely applicable for your location). The major reason I bought my tractor was for mowing my 2.75 acres (mix of pasture and yard) as even with maintenance I was generally getting about a year of use for every $1000 I spent on mowers from big box stores (without being able to mow the pasture). For me in this area a year of mowing tends to be ~50-75hrs of mowing (i.e. everything needs to be mowed at least once a week, if not twice to keep from becoming a jungle). Much of that is in hotter weather so the air-cooled engines may not have been able to cool themselves as well.
Depending on how comfortable you are with having the mower behind you (and if you want to bag the grass), I'd actually recommend looking at a 3pt finish mower as at a certain width they become the cheaper tractor-mounted mowing option, and rear discharge becomes a more common design (which can be helpful in avoiding/eliminating grass clumps). I'm sure many will disagree with that, but it is a very viable option and for me has actually been the superior solution (have had big box tractor-style and zero-turn mowers) though it does have a bit more of a learning curve (e.g. need to flow around obstacles like water does branches/rocks in a river instead of driving circles around them).
Personal opinion a heavy-duty/high-quality rear/scrape blade (for snow removal & driveway maintenance), a quality finishing mower (can handle tall/thick grass if you slow down, use less than full cutting width, with a high deck setting), a bucket (snow removal & general carrying/digging) and set of pallet forks (very useful for carrying & unloading) would likely work for starters. I would also recommend discussing the costs of having the additional hydraulics added to the tractor at initial purchase vs. later with your selected dealer for your selected tractor as grapples on the loader, and rear hydraulics can make tasks quicker and easier. ....and I'm of the mind that using appropriate machinery can help save the body (and prevent resulting medical bills).
A rotary cutter would make a nice addition, but having used my finish mower on thick (dripping) wet grass that was 12"-24" tall I can say that a finish mower is able to cut such grass though it's far from the ideal solution. In thick grass my own thoughts run toward having no more than 2"-3"-ish of mower deck width per HP (at PTO). More power per unit of width can help, but less just causes more problems (e.g. using less than full width to get a clean cut on the first pass even at lawn grass heights).
..now as long as this got it might be a nickles worth of advice that isn't worth the nickel -- so feel free to value it as you wish
:thumbsup:
