Skirting's an interesting process. I haven't done it with a tiny home, but I have with a no-foundation cabin in Maine.

I've thought about just jacking it up and putting an actual foundation (short frost walls and a pad), then lowering it back down, but it looks like a big job. particularly as I'm not sure I can safely lift it without flexing.

It seems it'd be straightforward to design a tiny house to be able to be jacked at the corners as there's already a metal frame.

Once you have a foundation space, you need to deal with things like humidity through the rest of the year. The best solution, which we have in our year-round home is a layer of insulation (styrofoam) under the pad, and, of course, insulation on the frost walls.

Also, crawling around in a crawl space to deal with plumbing is NOT a wonderful way to spend an afternoon. I'd like to think that tiny homes tend to be plumbed with PEX, which doesn't split when it's frozen with water inside. I ended up ripping all the copper pipe out of that cabin after a weekend of replacing one section, then another, then...