At a high level, this is generally the path people take - we see a lot of people have success in this route - start building the portfolio with banks, low down payments, and then **generally** when you hit around 5 or so properties - it starts to make sense to switch over to LLCs, its too hard to qualify/deal with paperwork of banks and switch towards private lenders like DSCR Loans - (LLC friendly, easier) to scale past 5 or so.

And one other, and what brings me here, is hit and miss.I emailed this company, and the initial response only took 1 day to respond.

He could get hit with a significant expense and not have the funds to pay for it because he hasn't collected enough rent income.

To hit on a few points you made - the first around "how long will this last until regulations catch on?"

Loan to value ratio: The higher the loan to value ratio (LTV) is, pricing takes a hit.

Doing this will accomplish:1) Show to your boss, so he better understands what you do and how valuable you are2) You can create some training guides3) This is actually #1 - figure out more efficient ways to do things!

Can anyone recommend a training program that I can do so I can hit the ground running. 

Hit me up if interested.

What about keeping it way it is and hiring a PM.I would either option A or option C and lean toward option C, while take tax hit etc. and others its done and do not need the mental strain

That's what I did.I'm not saying don't go for condos, but really do your due diligence on the HOA to make sure they are in decent shape so you don't get hit with bills later on.