Snow removal might be nice. I know this may sound stupid, but I've never needed to buy a riding mower lol
Not stupid at all.. you just haven't needed one before now. I would take the Mrs., and just slowly walk the property together and discuss any ideas or goals you may have (other than the physical structures). As northerners, having the ability to move snow in bulk is a BIG thing to consider when plunking down many thousands on a tractor.
Even then there's considerations.. would you want just a simple plow attachment, or maybe a bucket that can do the same thing while also being able to move earth if needed. There's even snow-blowing attachments. That's why you need to start looking and potentially planning your long-term goals for the land too.
If you're not looking to develop the land much beyond where it's at now, I'd look at a pre-owned rider with at least a 48in deck. General rule of thumb is to start considering riders for 1/2 acres and up. Tractors are a big deal here in Wisconsin. We have all the farming along with a shit-ton of annual snow (a known meteorological term here).
I have a buddy who's sold Case and now works as a John Deere sales manager. The return rate is huge... not because they suck, but because people bought too small. So there's a great pre-owned and secondary market (usually). Maintenance and repair on most anything made these days is pretty straightforward and inexpensive. Especially with all the DIY YT vids now.
I agree with
@Hixs on motors.. and especially on hills. At age 13 or 14, I ditched a JD tractor when I lost control on a hill. I wasn't hurt and the tractor just tipped on its side with no actual damage. I doubt I'd be able to make the same leap today...
Which brings me to roll bars and pressure switches. Even back then, the pressure release (killswitch) off the seat stops the blades abruptly and kills the engine. You mentioned having hills, keep that in mind (depending on grades of course). Also, if kiddos, strict yard rules when mowing: if they're outside, they MUST be on the opposite yard of you. If mowing the front, they can only be in back, and vice versa. I've put pebbles through siding before from mowing.
Look for torque and don't get sold on HP numbers.. a common sales tactic used on Joe Blow homeowner. If your mowing land is mostly obstacle-free, stick with a simple steering wheel. If you have to do a lot of maneuvering, opt for a zero-turn radius mower. They're pricier, but way worth it. I'd also look at a bag, even if your plan isn't to bag clippings, I'd still look at one that has it available. Carts are a nice option as well and will get used more than you think, but they can be had used and cheap.
Creature comforts: definitely a cup holder, definitely a HIGH backrest, and foldable arm rests. A hydrostatic tranny is nice too if found at a reasonable price. Smoother ride and shifting, quieter, more responsive.
Keep in mind that just about everything is more expensive right now. If you have a Home Depot card, they always have some kind of promo with it.. and the more you spend, the better it is. It'd be a good place to start if you're not buying from a dealership.
Lastly, if you decide you want to finance, contact the lender you just used for your mortgage first.
Provided you borrowed at a decent LTV, they may be amenable to tacking on an asset related to home maintenance and upkeep at your closing rate. Just make sure to knock it out as fast as you can!
Whatever you end up deciding on, keep us posted and let us see some pics of your new hog!



