That said, you can easily live for free while your tenants pay your PITI and pay off your property for you. 

I don't know south FL very well but I would think you could find something easily.

Is this something that can be determined/estimated easily and accurately before talking to the seller?

I'm glad you were able to rent your 4/2 easily, good luck with renting the 1/1!

It is a second job. with all that said you  have holding costs every month. if the loan pmt is 400 and it took me 6 months. that's $2400 holding costs. not to mention utilities, taxes and insurance could easily add another 2000.

At the end of the day I am just really curious to know if this strategy is even worth the hassle, and if it can be easily replicated so long as the seller wants to sell bad enough and the property has been on the market for a significant amount of time..

You could easily spend 6 months worth of rent between turnovers just if you had to repaint.

The detail person can't get to the big picture, until they've worked through all the little details and they will easily get hung up on things that may not be a perfect fit.

the number looks great, but if it's not in good area, you'll need to spend $2-3,000 easily whenever the tenant moves out.

I have a first loan at $384K and I'm looking to get a HELOC (home equity line of credit) for between $150K and $200K which would still keep me below a LTV of 80% pretty easily.