While not ideal, this was expected and I baked that risk into my objectives. 

I always issue the notice to pay or quit (called various things, thats what it is here) the first day that rent is late, just to start the process in case they don't pay, so you can get them out as quickly as possible and start fresh.

I would find yourself a better inspector and bake these things into your deals or walk away. 

Clean it up, put on a fresh coat of paint, and list it on the MLS to attract tons of buyers, including retail buyers!

Most tenants already understand that some of the utilities are covered by the landlord, who in turn will bake it into the rental rate. 

If you can find ways to save them money on their taxes, they will help and teach you.Most people looking for mentorship now don't know what value they can offer, but yours is baked into your profession.

  $2,500 for an updated place / fresh paint & finishes.The house is not updated, and could use paint, etc. so I am reluctant to adjust too high too quickly. 

When I ask for reasons I get cost of living, quality of live, moderate climate, fresh water access, no natural disasters and moving back to where they were from.From what I can see the trend to the Midwest is steadily increasing, but by no means as big as moving south.

In essence, this and dozens of other attributes are all baked into the cake long before I come close to acquiring it.

The cost per booking is baked into the guests charge of staying at your STR and if damage is done the item(s) are replaced or fixed at no charge to the host.