The fact that you asked the question showed that You are very smart.

If they need money choices are reverse mortgage (not a recommendation, just an option) or sell.  

If you're looking for financial freedom, cashflow is your better choice.

If you think that is too much, then there are a lot of duplexes in Lakeland which is a good choice if the price is right.

I was leaning towards declining the deal even before writing the post but I figured it’d be smart to seek more advice.Regarding the car loans.

I agree with John, as long as you have someone to call for any issue that may arise, then you are good to go.Make sure you have smart devices like locks and thermostats that you can control from your phone.The most important person you will need is a reliable cleaner!! 

You simply have to close your sale before closing your purchase.Your thoughts on only purchasing a couple of properties and then doing a cash out refi is also very smart. 

My favorite quote from that book is"Anyone who dreams of an uncommon life eventually discovers there is no choice but to seek an uncommon approach to living it"  - Gary KellerTo be successful you can't just copy what someone else is doing exactly, and you don't need to come from wealth and connections in order to be successful in real estate investing.  

As an investor, I had a choice to list any way I desired and I never desired to use the MLS to list my units.  

There's no "rules" regarding who has to be on the lease, you can make your own choices but adhering to common practices is probably wise.