Touring Show Questions

I want to get into the business of working on touring shows. I would like to get some more details before diving into that world.

1. I am on a medication that gets mailed to me monthly. How does that work if I'm on a show/the show is on the road/there is no fixed address?
2. How long on average does it take for a person on a touring show to get Union health benefits?
3. I'm currently working with a UFCW local what should I tell my current union when I leave? Doubly so if I need them for health insurance for any overlapping time between me leaving that union and getting into IATSE?

EDIT- So sorry I feel like an idiot, but I would be going into the tech side I assume that will probably change your answers.