It's oil based and costs $20 a quart.

I'm an Architect and Builder based out of Watertown, MA.

How are you going to touch base with them? 

I've seen too many people jump in before gaining some base knowledge.  

3) Should I get lending from a FL based lender or San Francisco Lender?

the biggest issues are that the available tenant base drops dramatically around October and doesn't pick up again till the end of the school year.People are no different than animals in that regard.They want to be settled and hunkered down in a property before the school year and/or bad weather starts.Quality tenants with good financial backgrounds don't want to move their families in the middle of an icy,snowy winter for obvious reasons,and good college students have already started school in August.Many of the few available tenants will have questionable backgrounds like recent job loss,previous eviction,bad credit,difficult income verification and don't make 3 times the rent,criminal records,etc.   

My math showed it is a 9 cap based on actuals and will be a 13.5 cap after it is re-positioned (market rents, sub metering water).

If it is very large you likely need to contest the EM be returned to you.Did you not give cancellation notice based on a finance contingency in the contract?

Your compensation structure MAY very well be a combination of base pay plus comission, perhaps in line with the industry average.

You need to make the decision based on business reasons.