Too many replies to quote, so thank you all for the advice, we are definitely learning a new way of life.
Our situation is a bit different because I have acquired a blood disorder which leaves medically retired. I am liquidating some assets I have had set aside since I was 18. I had hoped to keep it growing, but my health issue is forcing me to change my lifestyle or die. The tractor will allow me to do many things on my property without being sent to the hospital, again. My wife is the primary bread winner because of my disability. She has no issue with this and is happy to finally be the one to save the day. She's a nurse and makes decent money, soon to be more once she finishes her education.
We considered a plow for the Dually, but only after we get a third car. She has a Fiat 500 Abarth cabrio that was purchased several years ago without the intention of going to such a rough environment. I bought her a set of wheels and snow tires for this winter, but wish I had gotten them studded. I don't know if she can fit chains because we went slightly larger on diameter to give her a bit more ground clearance. By slightly I mean 3/4" on a new set. Either way, I have a third set of wheels for her car in NC that will be retrieved before next winter to have a set of wheels that have studded tires. We will swap on the studded tires before storms and swap them back out after the roads/parking area has been remediated. The third car might happen before next winter, if so that will get the studded tire treatment and the Abarth will be summer only.
After mud season we will begin constructing a pole barn, initially with just a dirt floor. It will be at least 30' wide and we will add length as we go and then summer 2020 get a slab poured after we finish the length. Eventually this will become a finished wired and heated workshop with covered parking on the sides (because I want a wood stove inside for heating and also insurance). I will also purchase a Logosol M8 landowner grade sawmill to construct said building with the trees we will be clearing in order to have space to build the structure. The tractor will make it possible for me to build this structure as if can lift and set posts, lift trusses, level the ground, etc. I want to at least get a 30x20 structure built so we can park our vehicles and have a place to put our sand for next winter. Ambitious I know, but I am retired, so I have plenty of time.
We have several buckets of sanded salt to get us by for the time being. I knew our first winter would be tough, but we have experienced setback after setback. My transfer case lever on my truck popped off of the linkage so now I'm stuck in 2H, which could be worse. The truck is parked at the bottom of the driveway because it's too steep and my bed is currently empty. It's going to the shop on Monday because I have nowhere to work on it currently, which is why the pole barn is getting built eventually. The stove that came with the house had a giant crack, plus it was way too big for the house anyway. The previously mentioned damage that was hidden from us. We plan on pursuing the seller's agent since they didn't disclose damage they were aware of. The house took three months to close, so we got here late. My wife's car is stuck, but at least my truck made it out of our skating rink to get her to work even without 4x4. Even with all of this chit that went wrong, we still love it here and plan on staying here forever.
For those that are curious, we live on the eastern side of Machiasport across the street from the water. We are less than an hour from Lubec, the most northeastern point in the continental US. Somehow Eastport claims that title as well, but that's only a longer drive because there's no direct route from where we live. The bridge is on the north side but we live south of Eastport.
You can't see the water today because of the rain, but this is from our bedroom sliding glass door.