By sending a check, in many states, if the tenant cashes the check they are de facto agreeing with your damage assessment and will have little ground to dispute your accounting.  

Double check to see if that works.

Below is the factual data.Rental Inventory & Median Rental Prices (The data is for Ft Myers and Cape Coral)As stated in previous updates throughout the year, we were expecting an increase in inventory and a decrease in rental pricing.

One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions. 

In our situation, property managers won't likely fit into the pie since we are looking to sell the property in the open market.However, you can always leverage your "rock star" agent who found you the deal (assuming it's not an offmarket deal or from a wholesaler) to check up on the construction every so often.

Let me check on shipping, specifically for Hawaii

That is a data/privacy issue that could cost them millions.

Or is there anyway we can do some background check on contractors to see if the contractor is legit?

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Pls reach out and check your PMs!