The "Live and Flip" idea could work if you're okay with a short-term plan.

Many people who choose to self direct their retirement funds choose to become a private lender and either go through brokers who pool money together and loan short term to fix and flippers as an example. 

That redemption period runs for three years after the investor takes possession of the property. 

Long story short, it hasn’t gone great so far, and I’m in need of guidance and mentorship.  

His short videos are gold.

I believe it will barely break even and in addition to that, I wouldn't be able to afford an extended vacancy period either as that will require more reserves than I have currently available.

No bank allows a family member to be the buyer in a short sale.  

I find my deals off-market and do some cosmetic updates.In short, it's not for everyone and many will fail trying to run this playbook from out of state (or even locally).There are still areas and markets that work, you just need to be more creative or willing to put more work in than you did in the past.

Thoughts on investing in a STR in Reunion Resort in Orlando, Fl?

I tried to explain to him that when a Landlord first purchases a property, the first two (2) years are the period wherein you find out all the problems and quirks with the property.