I have every intention to self manage this for the duration of my career so there was a bit of selective over sight on that particular expense.

If you can shrink the duration of the  financial burden by providing extra cash, I think that would be preferable to reducing her payments.Good luck!

@Tim Clark you don't really indicate the duration of the rentals to "family & friends" - these rules don't prohibit terms of 6 months or longer.

This is true if the duration is 5, 10, 20, 30, 40, 50, 60 years; it does not matter what number of years you want to start the basis at.I do not know your current living situation but knowing that I am pro investing local this is what I would do: 1) Look for a detached duplex local (in OC) that has sweat equity but can still qualifies for an FHA loan.   2) Purchase the detached duplex using the FHA loan (at 5% of FHA down your $50K will go a long ways) and house hack the duplex living in the more thrashed unit 3) Rent the "bettter" unit while referring to yourself as the Property Manager (not the owner) 4) while you live in the more thrashed unit I would work on earning the sweat equity (rehab the place) 5) when done rehabbing the more thrashed place I would consider if I want to keep the tenant of the other unit. 

Mortgage it subject to bank limits and payoff duration limits, and use that full loan amount (loan principal is free of income taxes) to do another project.

The duration of the investment will be for 30-years - or until the Home Buyer pays off the Note, whichever comes first. 

So for the duration of your loan, you should be able to anticipate your mortgage payments and to make projections in line with our objectives.

This means your total payments maid during the duration of the second loan will not equal the total amount owed.Doesn’t really seem like much of a bonus to me.

Duration 6-12 months.

But you can't get another FHA loan while you have that one, and you are stuck in the FHA for the duration of the GNND.