Mulch or Ground Cover: For the back, you could lay mulch or gravel temporarily.

I believe you can offer her a renewal at $2,000 a month, she won't be able to afford it, and then you have legal grounds to terminate her lease.

It rained a lot here creating soggy grounds and then the winds came, which knocked down a ton of trees and power lines.  

The ones who haven't heard about it seem to not care much or are grateful to be informed of the "changes".We are getting less objections when presenting the exclusive agreement than we were prior to 8/17.

Being an agent will take a year or so to get off the ground so be prepared if you go that route.

Hiring a bookkeeper to watch the income/expenses is like hiring a gardener to tell you how many roof shingles are laying on the ground after a wind storm instead of hiring a roofer to repair the roof.I recommend that you look for a quality property manager who can maintain the properties and help with the bookkeeping.Start by going to www.narpm.org to search their directory of managers.

I have seen properties get ran into the ground when being rented this way with poor management. 

You are creating a new job for yourself.With the number of STRs (I assume that just because there is 850 permits doesn't mean that they are all in use), plus the in you have with the other owners and the local page, make it easier to hit the ground running.Maybe you reach out to some of the independent contractors you know and ask them if they might want to join your team.

In my area , you would have a minimum of 1 year from the time you bought the land until you could stick a shovel in the ground .

The key is to find a middle ground where you’re mindful of spending but still allow yourself to enjoy the present.