Not to add kerosene to this fire, but...
I am in a somewhat similar situation to you and I have to agree fully with Bob on this one. I have 2.5 acres of which 1 acre is somewhat thinned woods which I keep knocked down every 2-3 weeks. I also help mow another couple acres in the family several times a year which is pretty rough and a borderline bushhog candidate. I have wanted a tractor for quite a while and will purchase a sub-compact/compact tractor very soon. BUT, the point, and I believe others have also mentioned, is that I've managed pretty well up until now with only my JD335 which is not as substantial as some of my neighbors sub-compacts, but I also have an equal number of neighbors with $1000 craftsman mowers managing just fine. I have agonized back and forth between a sub-compact and compact for my needs. Part of me "wants" the compact due to all the known advantages, but deep down I think the sub-compact is probably the better fit and I can't deny Bob's logic which I've now read in multiple other threads. While I find uses and have endless yard projects over the horizon, it sounds like your needs are slightly greater than mine (little more land, more snow to move, longer drive (1200'?), new home startup needs, etc.) so I believe your needs could easily justify stepping to the compact. Stepping above to mid is overkill and *could* cause some regret latter.
I will add a couple of comments to ponder which are nagging points for me in my decision to go up in size and you can extrapolate to the mid category. Some of this has already been touched on by others:
Maneuverability and size/weight are concerns for me. This includes fitting in tight places and close to objects/trees, increasing time to perform tasks, and also increasing the odds of tearing up the yard. Remember turning around using the forward/back maneuver requires cutting the wheels from one direction to the other; add big tires, heavy weight, and potentially 4WD engaged and you have recipe for trouble. I know many here with larger machines say they don't have compaction or rutting issues, but tearing up one's yard is also very sensitive to soil and grass type so you will need to decide yourself. If you have areas (low/flat) which tend to stay moist, you will be prone to having trouble with the heavier machines. Many people, particularly further South have grasses (e.g. Fescues) which can hold up to almost anything. Myself, I have bluegrass which wants to be pampered a bit and under some conditions I must be careful even with my 650lb "lightweight".
The bigger machines take up more space. Storing multiple machines, leaving the tractor outside, or building a shed is not an option for me (as edicted by my wife). If I want to add something to the garage, something else is sacrificed. No matter how large your storage capability is, in 1 year you will wish you had more. You may snow blow/till few times a year and mow 30 times/year, but that tractor will be taking up valuable space 365 days/year.
Will the machine need to be moved often? If so, then a bigger trailer may also be needed. More cost, storage usage, and difficulty moving. Also, this may dictate or restrict future vehicle purchases to pull the bigger machines. I am sensitive to this as I really don't like the idea of trailer sitting around and today my JD335 fits perfectly in the bed of my truck (although putting the 54" deck in with the tractor is sometimes tricky by myself). You may find just getting a 72" MMM into a truck bed is job for 2 men and a boy.
Almost everything will be more costly on the bigger machines, whether changing oil, fuel costs, filling tires, general repairs, etc.
Resale value is regional, but around me good used smaller frame tractors are easier to sale than larger tractors.
Finally, would/could one's spouse be comfortable driving the bigger tractor? If you travel much for work like I sometimes do, knowing the wife can clear the driveway (in emergency) is reassuring. (I realize one doesn't want their iron steed to be too spousal friendly lest ye find yourself in competion for seat time or end up doing the yard edging while the spouse tools around the lawn on your toy)
You may have a bit more flexibility with a new home property in terms of planning your landscaping, fences, gates, etc. to be more tractor friendly, and if someone never evaluates the sub-compacts they may also never regret an encumbrance they may be dealing with. I realize everyone's situation is different depending upon needs, landscape, storage availability, etc.; so again, each will need to set their own priorities. There will always be that every other year project where something bigger might be nice, but I'm confident you will have more 10x more instances were you will be glad you didn't.
Good luck in whatever size (or color) you choose,
ADin (Still undecided myself)