A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

You increase the likelihood that you continue to receive that $8,500 each month. 

It would be great if your rental could also work financially as a long-term rental if the STR market changes.  

*As a side note, I think maybe it would be fun also to try and identify where new technology or machine-learning driven approaches could increase efficiency in the spaceAs for my financial situation, personally, I have around 50k saved but 20k of it is tied up in assets I don't want to pay capital gains tax on.

The first couple is a no-brainer.The second group has too many people, increasing wear-and-tear on the home.

I gave Financial Freedom my credit card info so that they could bill me $3.95 to ship me a book.

They literally went through each operating agreement and prepared an email listing out each member of each LLC and clarifying they each had to guarantee the loan despite the fact none of those entities were even being used for the purchase (which was previously explained to Dominion Financial). 

If you spend time learning how to manage well, your income will increase, you'll save time, and you'll maintain your sanity with the courage to expand.

It seems where you've chosen to move doesn't line up with your goal of reaching financial freedom?

My terms are identical to yours as far as the 1-year lease with 3 options to renew (for them), 3% yearly rent increase, etc.