I’m about 4 years from retirement and regretting not venturing into this world sooner.I’m currently going back and forth on whether to focus on short term rentals in Florida (Destin, PCB) or long-term single family homes in the Birmingham, Al area.

A HELOC is best used as a short-term debt instrument. 

Below are the figures:Purchase Price: $225,369.78ARV: $199,000.00Mortgage Balance: $209,099.44Great thing about wraps, however, is you can add equity, interest, and your own terms, which is what the borrower did here.Via adding $101,000.00 in equity, the borrower plans to sell the property for $300,000.00 for a 30 year amortization and have the borrower place a down payment of $15,000.00.

Flips are typically 6 months or less 30% ish , how much faster do you want?

Since your family member is paying the PITI, there could be questions about whether these payments constitute rental income or gifts.If you're the legal owner, proceeds from the sale would typically go to you.

@Fabian Escobar we typically advise clients to create a separate LLC (holding no assets) to act as management company for purposes of creating privity between that entity and the series LLC (which will hold the assets).

But really, you need to talk to attorneys, brokers, potential investors (typically will be friends and family to start), lenders to get real world feedback on what you need to do.

Currently being used as a short term rental.

A third party likely purchased that debt from the original lender (uncollectible by typical debt collector standards) for pennies on the dollar. 

In the next couple of years I will look at whether the long-term appreciation approach is practical.