Doing what you suggest would add virtually nothing to the insulating value of the walls, and would cost a small fortune.
Some questions:
1. Do you know whether the walls are built with 2x4 or 2x6 studs?
2. Do you have access to any attic or roof to add more insulation there?
3. Is the main floor over a typical old Poconos crawl space? (such as one with unparged and un-dampproofed foundation walls, a flimsy and ineffective vapor retarder, no concrete floor slab, inadequate vents, soaking wet insulation, a fair amount of mold, and some rotted structural members, but other than that, everything is OK)

)
If the walls are already insulated, I would try to add more insulation elsewhere if it can be done easily. I'd guess that with a loft, you have vaulted ceilings, so the roof is not going to be an easy place to add insulation, but the floor would certainly be one, and if the second floor other than the loft has a flat ceiling, you could add insulation there.
Do your windows have insulating glass? If not, money would be well spent either on replacements, or on storm windows. Are the doors insulated? There is amother very small improvement, if not.
Another good place to spend money is caulking and sealing everywhere possible. The power company often will do a survey of your home, to identify places where energy (particularly heat) can be saved. There are also private companies that will do an infra-red scan of your home, which will identify sources of heat loss. Do one or both of these studies, and then you'll know where to caulk and seal.
If you really want to change your siding to vinyl, then you will have to remove the clapboard and install sheathing, which could be insulating sheathing, adding some insulating value. The flimsy little backer boards they install with vinyl siding are virtually worthless for insulating value.
I would guess, from my limited but growing experience with older northeastern Pennsylvania homes, that the biggest gains can be made in the crawl space, and any attic spaces.
If you'd like me to take a look, no cost no obligation, I'm in Tobyhanna in Monroe County, and I'd be happy to do it. My email address is rhetzel@ptd.net.
Architect (NY) and Home Designer (PA)