Looks like for now, blocking the crawl spaces is in order. Come spring, it may be prudent to just knock those interior walls out and make the crawl space an interior space, insulating as necessary.
Caulking helps with drafties all winter, but it's certainly not a permanent fix for large gaps. It will eventually shrink, crack, etc.. The proper fix is usually pull the culprit boards/trim and fix/replace them. Unfortunately, this will usually expose more problems with each board you pull, and it can really snowball, which is why you only do one area at a time. A full remodel is NEVER a necessity, as some would make it seem. If there were enough damage to require a full remodel of an area of the house, you shouldn't be living in it.
The plank constructed door can be a really elegant thing if done correctly, but when you can literally see through the gaps all around it, it's probably not so nice. Assuming it opens outward, you can crawl into the space behind it, make note of where it closes, and add fur strips around it's perimeter, with weatherstrip sealers on them. You can then stretch/hang a layer of plastic on the door, and then stretch/hang an old blanket on the back of the plastic. The plastic could be an old garbage bag, if you were so inclined. (I reuse my garbage bags, cuz I'm cheap, so I've always got an "old one" laying around.)
For now, the crawl area that has no real door over it, you could just remove the door altogether, screw a board over the top of the opening, and hang a heavy sleeping bag or canvas tarp over it, making sure it's tightly fastened around the sides and top. This, of course, assumes that you don't need access to that area over the winter.
Water heater, see if you can get some cheap salvage insulation from a neighbor's remodel, and make yourself an insulation jacket for it. Make sure you also give it a hat and boots. Regarding the other water heater (that isn't hooked up) at some point, you could use it for heat storage from the shower drain or similar waste heat source, or you could use it for a Johnny Appleseed biodiesel converter, etc... there are many good uses for it.
Unfortunately, with light switches and fixtures, either gaskets or caulk are about the only proofing you can do, that I'm aware of. In some cases, you'll want to use both.
Regarding the water heater again, if it's any indicator, your pipes really need insulation, as well.
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