I think that the market for short term rentals up here in the summer is great but in the winter it mostly dries up.

While I hope to purchase it, even if I don't this will be a good dry run.

If you really want to renovate NOW then offer her money to leave, otherwise I would let her be and terminate at the end of her lease. 

Especially if they are dried first before you install them.

The only way the sale wouldn't go down would be if there some obvious contamination which there isn't, or a bad cleanup job which could be fixed; the offer's pretty cut and dry in that regard, and I know others who have gone through the process with no issues (none of them sold a residence, they were just holding raw land). 

Dry-cleaners of course can pose a significant contamination issue with a property, but would a regular self-serve laundromat have similar contamination potential?

For joists you are looking for anything with dry rot, bowing/splits in them, or sistered joists (shorter joist screwed/nailed into the other for support).

Dry rot on siding. 

Bases get closed occasionally, and you don't want a base closure to happen and your rental base to dry up as well.

Hello there,TL;DR, I want to invest $100,000 per year as downpayment on 3/4plex as a primary resident, which city can give the best cashflow?