I screen tenants over the phone as much as possible and I schedule all showings back to back so tenant only needs to clean once.

We are having to change our coverage due to the short-term rental not being covered by my current insurer. 

When we identify a problem (for example: a fire hazard in the electrical panel) we'll recommend a specialist (an electrician) to fully evaluate the problem and prescribe the most appropriate fix.Back to your specific question:  if the basement walls and ceilings are covered it will be difficult for anyone (including a structural engineer) to evaluate for structural issues. 

Would you cut your losses and sell the property OR raise the rent slightly to cover the mortgage and continue to build equity in the property?

So,...if your rents, less vacancy allowance cAn cover your taxes, ins., repairs & maint., plus a satisfactory profit, then go for it

Enough to prob cover the bills for 12 months.

Do you have any text messages that you could screen shot and print to keep in property folder?

But yes, you basically want your lease to cover these situations.  

How would you handle this situation (besides better screening)?

(Just make sure the mortgage you're willing to go for, you can cover with out renting it out at all.. that gives you full control and all the gravy).4) The flipside to #3 is that you rent short terms when you're not on the road.. it may not build equity but it would be a place you could call home until you have to hit the road again and the money you save on land taxes and maintenance could be placed in an account for a good sized down payment for the place you want.Main point is.... your "dream house" generally isn't an investment.. it's more like a forced savings plan that may appreciate in value.Real estate investing isn't every about buying your "dream house" because others will be living there.... dream homes and tenants don't work.