If, in principle, I can make it so that I have extra income left over after deducting all expenses, I have a positive cash flow.

Absolutely find another CPA that knows the STR rules and puts you in the best position possible in the event of an audit.

Ideally, the Borrower would make a single payment like they are used to and my Investor has security based on the hypothecated Note.Or, must/should I have Investor in 1st position with a Security Instrument and Note based on agreed to terms and then create a Note Rider for a Wrap Loan between my LLC and Borrower spelling out those agreed to terms along with a 2nd Security Instrument in 2ndposition.Example:Borrower Pays: 12% and 3 PointsInvestor gets; 8% and 2 points (spelled out in a Note)LLC gets: 4% and 1 pointPerhaps there are a number of ways to skin this cat but I’m looking for a simple, yet protective, approach for both Investor and LLC.Thanks,Steve

They  refinanced after it was rented out, so they were all in for 158K between loan and downpayment and 77K in forced equity.

Hard money lenders are not going to take second position to provide a down payment on another loan. 

I have found a few homes where the numbers work and were in the positive (barely).

I will likely want to live in the home for two years to avoid long term capital gains before renting out the unit & using the equity to purchase another property for myself.

The goal is to build equity in property quicker to eventually cash out re-finance.

It currently has about $200k in equity.

The HOA fee is 50%-60% less than comprable condo buildings built within a three year time frame of the condos in this deal so I'm pretty sure that once I see the HOA's financial position, I will see that it is under funded.