This is something I routinely struggle with in my rental business.

I was actually thinking it was for landscaping and doesn't look like they do anything fancy other then mow.

If you can't get that fancy, at least use DocuSign or similar to get digital signatures, and if you are in Maine, don't forget all the compliance docs: Radon, EFF, Lead, Bangor Tenant Rights (I see you live there). 

From my understanding insurance doesn’t cover this, so we essentially had to factor it in to our overall investment decision and weigh the risk against our projected returns 3) Routine scenario where we have to cancel reservations during evacuation times.

In fancy economic speak that's called INFLATION. 

All of my life has been built around a routine.

Do they perform routine inspections? 

We have always been content and grateful with what we have, even when we were sleeping on the floor and adding scrambled eggs to our ramen noodles to have a “fancy” dinner.

If your whole day is that full that you routinely can't get the rest that you need then you need to find a way to outsource your most repetitive tasks through employees or technology. 

Something about a Realtor needs a fancy vehicle to be deemed successful.