While I appreciate your thinking outside the box, I think you will find when all is done and said, it's not cheap and it's not comfortable.
- I would assume the RV is a total loss when figuring your costs. It's going to get hard use in tough conditions. How much are you dumping into it if you need a loan? Assuming you are buying used, do you have any experience? Most people will miss significant issues, so your odds of getting a problem rig are higher.
- Electricity isn't going to keep up heating with even a smaller Class A. You will need a functioning propane furnace and even then it's marginal. We were caught in a cold snap in New Mexico once and we were going thru a 30# tank a day and it was only able to keep the RV around 60F. We had a pretty good cold weather setup.
- Dump stations and outdoor faucets will be in short supply in the winter. Most people don't camp in the winter, so there is no reason to maintain them in the winter.
- Storage lots in the midwest run $200-300/month (and you can't stay in the RV). I would expect in a high end area like Connecticut it would be at least as much or more. HOAs (Home Owner Associations) tend to look down on RVs even being present in driveways, let alone someone staying in it long term. How urbanized is the area? I can't see anyone in an urban/suburban area going for this (or being allowed by zoning/HOA rules). If you can get out to more rural areas, you might find a farmer would rent you space behind the barn.
If you were somewhere down south, where you deal with an occasional 20F night, it's much more doable. If you are dead set on this, I would be looking small & cheap. A small Class C with no slides (under 24ft) will be easier to deal with and take less to heat. If it's only you, the space from slides is not so critical. If you can find a campervan, that can allow you to be a bit more stealthy but does significantly impact comfort (still maybe acceptable for 1 person). Even a small under 20ft trailer would be easier to manage but again, it comes with limitations. I would limit the search to what you can pay cash for.
