Sounds like a great set-up right there Eugene. I like the well made trailer bicycles for families because they keep everyone together and everyone can help according to their abilities. I have one hanging on my porch from before my divorce (and I honestly hope Ex2 picks it up because her little girl loves riding that thing).
I was doing some research this morning on dog sledding and I discovered that dog teams were, historically, small in size (1-4 dogs) and used large breeds such as the Alaskan Malamute - what I'm considering doing. Sled racing created the Alaskan Husky (not a recognized breed) which is smaller and faster but does not have the pulling power of the larger dog. There is some good info at this website: link
As far as going the actual sled route, that is something that I would have to take as it comes. Bikejoring and skijoring are where I intend to start as bikejoring doesn't add any issues to the BOV during the summer beyond harnessing the animal(s) properly and adding their gear (mainly food) to the bug-out kit.
I'm also kinda in a toss-up between going with an Alaskan Malamute or a Samoyed for my first dog. A Chinook would be really nice from a sled-dog point of view, but with a population of under 1,000 I think they will be too expensive. There is a whole lot more than just "I wanna sled dog" going into this as the first dog is most likely going to be primarily a companion/watch dog.
I'm still thinking that, dog sled or no, a snowmobile is something definitely worth having when I first move north. It doesn't have to be some race sled nor does it have to be something that is top of the line, I just need something that can reliably get me from A to B and back on unploughed roads if I decide to take a rural newspaper route. I like getting up at 3am and going to work for a couple hours - it gives me time to discover what I'm going to be able to do that day physically and mentally (that disabled vet thing again... what a PITA). Where I'm at is about the southern edge of reliable recreational snowmobiling. I have a feeling that where I am going to is where they start to become work vehicles. Because of this I think I'll get one my youngest boy's senior year in high school and get some ride time before moving north.
As far as acreage goes, the plan is to find me about 5-10 acres with deeded lake access (not lakefront - way too expensive and I've been in too many flood events to trust living on waterfront property). This puts me on my primary and secondary bug-out routes and will allow for a raised bed garden (soils are poor in the region) and room to play around on with my trains, landscaping, a few critters (not livestock), and maybe even put in an archery/gun range. Once properly fenced in I think the dog(s) will love playing around outside in addition to the long daily walk.
The pickup truck and trailer have been reconsidered yet again. I'm seriously looking at just getting a Wrangler and a jeep trailer and being done with it. In the long run it will be cheaper I think. I just have trouble justifying the pickup truck when it's just me and it's not needed for a job or to tend a hobby farm, which got ruled out due to the new area I'm looking to move to.
I must be getting older and less active. I think it's kinda sad that a 95°F heat index will knock me on my butt.
One last thought: It is one thing to say that your choices are determined by your area of operation and household, but it is quite another to really think it though and see what you would think is a brilliant solution become a huge liability due to a change in situation. In my case divorce and moving the opposite direction of what I want to. Yeah, I still would like to move to Arkansas to be near my brother, but the summers there would completely incapacitate me. The summers where I'm at now are bad enough to force me indoors. Funny how -20°F doesn't phase me (I've ridden a motorcycle in it) but 80°F can make me physically ill.