I would like my first property to be a buy and hold to get some cash flow and go from there.

Taking a shot in the dark before I read any comments, to see where my own head is at regarding investor psychology.With the 1 unit already rented, it looks like your coming out of pocket $1,150/month.Plus $1,400 in SL and Car NoteYou have $20k in free cash that's not currently earning anything, but has the potential to earn $1,300/month or $15,600/year.That would mean your RR on the $20k would be 78% if you do the necessary upgrades to rent the 3rd unit.The $1,300/month also means you'd be living rent free with a cash flow of $150/month.

@Joseph YoungIn my experience billboards are always included in the NOI number which is then divided by the cap rate to give you a rough estimate of value, so to answer you question in short yes it should be included.At the end of the day, real estate has to be looked at as an investment you're buying today cash flow for tomorrow.

Didn't think cash flowing multi fam was possible within an hour of the city.

That makes your self-directed IRA investment passive (as it must be, under IRS regulations) but also lets your LLC handle the management expenses and receive a management fee to augment cash flows.  

You see, over the past year I have invested in 3 very modest but positive cash flowing single family homes in 3 different states.

(Investors usually buy duplexes for monthly cash flow which is small.

In most areas in Miami, prices are very high that it seems impossible to cash flow a property that you bought from MLS.

$26,000 a year for passive cash flow is pretty solid, if you 1031 the sale and you can get a return greater then $26,000 I would consider selling.

If you rent it out and the mortgage payment is less than the monthly rent income then you have positive cash-flow.