I gave most of my handguns to my sons and kept 3 which we carry with us. Check the CCW laws in each state as you enter. We'll be on the west coast next year and my Texas permit isn't reciprocal in CA, OR or WA, so while I'll have firearms in my "home", they wont be in the truck or carried on me. We've not gone to Canada yet, but from most of the Canadians we know, you cannot get handguns into the country (or it is not worth the trouble). We'll leave ours with friends in the Dakotas when we go up there and collect them when we return. We'll be going into Nova Scotia this summer, but are planning to leave the rig in the secured in a US Campground and just drive over for a few days and stay in hotels.
We're under 65, so healthcare IS becoming an issue. We see our doctor at home annually when we visit Texas, but getting care that is covered out of state is an issue for us. I'd make sure to check into this before you decide, especially if you'll be under 65. Medicare probably is more portable.
We belong to Escapees and use their mail service which has worked well for us.