Your is to educate them on the Reality of the comps, and what happens when they list too high.....property languishes on the market, buyers become suspicious/try to take advantage of an extended days on market, etc.

So my next three areas of research are:(1) To what extend does insurance on a rental property protect your personal assets?

I just wanted to extend an invite into our weekly mastermind!

One way is the seller could add a contingency on the contract stating they can extend closing by so many days to satisfy the exchange, therefore pushing back closing from the original date.

Is so, and they only charged you on what they collected it sounds like they are following the contract.If the contract and money owed is based on a duration of their time managing.

Then they have an incentive to economize on the duration of the shower. 

For example, in a high crime blighted area, one might expect the tenants to stay a shorter duration, cause more damage to the property than in a more upper middle class suburban area with higher incomes and good schools (where you could easily expect the tenants to remain much longer and cause fewer problems to the property when they do move out)... such that just looking at rental income relative to known costs (property taxes, insurance, etc.) might give one a skewed perspective of what the returns on each would likely be.

The tenant pays $2,700/mo for 7 years lease until I extend him or move him out to live there. 

Are there any lenders that would allow this to be put on the mortgage, so that I could extend these other notes out 30 years at cheaper interest? 

Some other subsidized loans require you to live on-site during the duration of the loan.