The real life experience is the best option for learning and gaining the knowledge you need. 

It sounds like you're in a pretty good position with some nice options.

We would offer more of a budget-friendly option which could include FB marketplace/goodwill -Manages furnished rentals (STR/MTR) for investors.

Your post about summarizes what I figured my best options are. 

Cashing out $400k and throwing it in an index fund is a viable option as well.

I think there’s some sort of option of to do a little refi on both house 1 and 2 and get the money needed to wipe out the line of credit(allowing for bigger flip opportunities, especially if I partner up with someone) and also renovating that garage space with the private investor as long as it is under 1000/month.

I look forward to your response and the opportunity to discuss potential options that align with your organization's leasing policies."

If not, they may want to speak to a mortgage broker local here in Florida to help expand their options! 

Sounds like I might need to follow Frank’s advice and consult an attorney, although that will definitely be the last option I pursue.

Cash for keys is a good option but it depends how much they owe.