Hi Alexander Owen, yes, to being able to buy the next property using FHA, but they will want you to refinance the MassHousing loan into a conventional product first.I actually used the exact strategy you are contemplating to start my empire 3 years ago.

however, the reason I was contemplating was I did not know if I have to up potentially pay $3500.00 (loan origination fee and everything to finalize the loan for the closing and ended up with buying the property).basically, I did not want to pay $3500.00 to get the loan of $20K vs. pay a smaller fee to get the HELOC which I could potentially lose this deal due to longer time to get it approve. 

And by a small operator, I am referring to contemplating getting started and researching whether this could be a viable and legally acceptable strategy for an individual looking to do a few deals a year, but potentially exceeding the magic state set number for private sales.

I just purchased a SFR in Bonita Springs / Naples (SWFL) area and am contemplating whether to rent it as a short term vs a long term rental.

Lance,Any financing you are contemplating using when the entity buying the property and taking title is an SDIRA must be Non Recourse financing.

I've contemplated hardwiring for security,but it seems most systems are wireless these days anyways. 

I'd only pay the monthly landlord insurance (roughly $120) and snow/grass.I don't have the funds to extend an all cash offer but am contemplating working with a hard money lender.

I have also contemplated the FHA 203k loan and living/rehabbing during my time there.

For example, I am contemplating having 50% of my mortgage payment ($400) come out of my direct deposit from my W2 employer, twice a month, into the rental account.

You are contemplating entering into a very high risk lease situation.