Your compassion is wonderful.On the other hand, we all must still be adults and meet our obligations even when we are facing challenges. 

Probably right, aiming for 1000 sqft livable space so not super tiny but still your point probably holds. 

The farther you get away from your hand, the more the whip moves.

You would structure the legal title such that each LLC holds a 50% undivided interest in the property as tenants-in-common.

I have about a decade of proptech experience (selling into CRE and RRE), a year of residential leasing for EQR and 6 years of resi buy and hold invvesting. 

He kinda "held my hand" through the process which gave me greater confidence.

Sad part is listing agents are advertising "FHA Assumable Loan" on MLS and they dont understand the process/timing.Is it better to apply for the FHA/secure the loan approval before searching for properties, so once a property is found, the financing is already in place without the 4-6 month hold up?  

You can camouflage the target on your back a bit by holding the title in a living trust. 

Even though the cashflow is negative now, would it make sense to hold the property for potential appreciation ? 

Investment Info:Single-family residence buy & hold investment.