If you can get a meeting with the tenant, ask her what she wants, find out why she's looking to stay, and if it's due to the rental rate, let her know it will be going up by $300 at the start of her new lease term.

So they only stayed a month or so every year.

At our property management company we are now writing all of our leases as 10-month leases, with 12-month renewals for those who want to stay and qualify. 

The lender taking the short will require the seller receive no benefit and staying in the house would be a benefit. 

I tend to stay away from trusts, because there is a lot to deal with usually (attorneys, parties involved, etc.)

Stay focused, solve these small problems and you'll be primed to solve some big ones next. 

Not an expert by any means but I stay away from flooded homes for now because no one is really sure of what the after repair value will be.

We like to stay for years, do most of our own maintenance, and the unit is deep cleaned and professional maintained consistently.

Put a lot of the little extras in there that don't cost much but that people appreciate for good reviews (a coffee maker with pods, an ironing board, a few snacks , a sixpack of local beer, etc).Also, I use Airbnb to rent out my basement apt to tourists and to find places to stay when I travel.  

Just stay true to your investment criteria and make sure that the numbers work when trying to remedy these issues and you should be ok