Excuse my opinions- they're just opinions, but I'm guessing you're going to want a larger tractor for the property you mentioned. I'll start with this; front mount snow blowers are iffy, especially compared to a rear, PTO driven blower. A bigger tractor with a front blade would perhaps be more useful. You are right about tractors, at least good ones, holding their value and not selling cheap. Sounds like you are informed about different used tractors' values, and features, which is all good!
Not sure if a MMM is ideal, but I don't know your situation, of course. Rear mowers seem better unless you're cutting a smooth lawn, and then, why not a quick zero turn?
It took me three tries to get my Goldie Locks' Kubota tractor- my first, a
B8200, was too small, and its gear drive wasn't what I needed (good for mowing large areas, but otherwise, no...). Second was a nice
L3130, bigger, heavier, not a lot of power but very capable if you weren't in a big rush, but too big and heavy. Lastly, a super clean used
L3400 (HST a must, for me I've learned), which had all the features I had learned I wanted thru my own experience: SSQA loader- which I wouldn't be without, rear remote, extendable rear links. All added by the first owner who had used the tractor simply for mowing almost all of its life, adding the new Kubota loader to it just before he decided to get a bigger Kubota. I no longer need it, but I have a 78" front snow blade that works well with it- (signature photo). (neighbor's groundskeeper has a one ton with a V snowplow, and he plows our lane- I just do clean up, and a bucket works for that). FWIW, tippy tractors benefit from simple wheel spacers on the rear- I added 2" each side, which broadened the rear end and helped with keeping it going straight pushing snow. Loaded rear tires help, too. I don't need to operate on hills, but when I do, those spacers give me more comfort. When I had to plow snow, I craved a heated cab, but a cab would just be a hindrance the rest of the time for me.
Long story short: buy a good Kubota, take care of it, and sell it for what you have in it when it's time to move up.