Have you calculated what your (monthly nut) is you need to survive business wise and personally?

Lenders often include a portion of the cash flow in the investment property as income to you personally to offset the DTI. 

Hey @Logan Barwick, I personally like option 1, but this depends on what your strategy is to grow your real estate portfolio.

JeffWe lead a couple investor meet up groups in person and live stream about the Central Ohio real estate market.

From a personal standpoint I target 70% LTV for any investment I have that way gives me ability to sell it if I need too

Personally, I wouldn't offer SubTo or a Wrap, For reasons I've written about fairly extensively. https://www.biggerpockets.com/forums/70/topics/1227199-the-m...However, I would sell on "Lease Option" and that may work for you.

Personally, my primary residence has appreciated around 6% in market value and I live in Levittown. 

I don't know if they still do it but if memory serves a few years ago TD Bank would do a HELOC on a rental in second position but only if it was titled in someone's personal name. 

I personally leverage, but have a large rainy day fund. 

It's not a personal sale between you and your son, but rather a sale from one LLC to another.