Fannie does have a guideline that allows a property to be deeded over to an entity so long as the original borrower is also in the entity, but you have to wait 6 months of seasoning and maintain continuity of ownership.  

I think that if you cash flow $300 per month, you are doing quite well, AS LONG AS you have reason o believe that no major repairs will be needed in the short term.

The fixed mortgage is what makes these deals not very risky as long as you know basic analysis and buy cashflow positive.

As long as they own it for at least 2 years. 

As long as you are coming out of pocket at around the same you would be renting somewhere else then you are still getting ahead in life because your tenants are helping pay down the loan and build your equity.You should also run an analysis putting in what the market rate rent would be of you did not live there.

As long as there wasn't a lien recorded on the physical title itself then there wasn't an issue. 

Any thoughts if an individual property can negative cash flow to provide capital as long as the portfolio is still positive? 

Things only have value as long as enough people agree it has value and are willing to bid against each other to obtain it.  

Late payments do not bother me at all as long as they paid all their bills.

As long as you have some residential areas where RVs and Boats are a pain to park or not allowed at all you will have customers.