If you want to manage a new business that you have no experience in, sure start it up. either way you better pay market rent to yourself or else you won't realize any gains in your CRE--which is why we are all here in the first place.

I could be mistaken, but I think you lose some of the income tax benefits of home ownership if the duplex that you own and live in is not in your name.DO you have a lot of assets?

I know I can ask my tax accountant, but wanted to get a general feel for what I am thinking of doing.This home was my primary residence for 3+ years then it became a rental for the past 1.5 years.How does the capital gains tax work?  

I took a similar path a couple years ago by utilizing the 203k and occupying one of the units - definitely HUGE benefits to that approach.I'm not as familiar with the Cape and Plymouth area, but one of my closest friends and colleagues is down that way and has acquired 5 multifamily buildings by starting with the same approach.

You just go get a license see if will benefit you. 

The benefit to this that although you may be paying more to borrow the funds, it would be a lot less headache than trying to piece it together with different investors.

Hopefully after all the hard lessons learned and knowledge gained from the first property, it won't take another 5 years to get our third.

The benefit(s) of diversification will likely get washed away in the cost of management. 

Did you ever make any progress in gaining any of this information?  

Again consult an attorney and/or accountant for estate planning, but one of the few earthly benefits to dying is passing on property with a step up basis meaning less taxes or even no taxes for the kids to pay out when/ if they sell they the property.