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

I’m based in the northern suburbs of Boston, so I’m looking in that area but also open to other parts of Boston/Massachusetts.

Cash out now that the craze is hitting main stream.

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.

You hit on all the key differences between banks and private money lenders.

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. 

Even if it isn't a perfect match it will be fine as the light hits walls differently.

That's hitting the 2% "rule", and if you can maintain regular rent on that you've really hit a home run in today's market.

It hits the nail on the head.