At the very least, he/she would likely be willing to pull a CMA for you, but keep in mind that it's likely weighted to your advantage.

The addresses in previous years were heavily weighted to lower value properties, probably reflecting subprime loans.  

So I'd suggest that you put some weight on and grow out some facial and/or body hair.

I buy distressed stuff at a discount that has been owned by slumlords or losers who do no upkeep or maintenance on the building

Differences in insurance premiums and upkeep for CBS vs vintage stucco?

Do you need to account for any extra expenses like water, trash, upkeep, etc?

But I'm nervous about all the added costs since upkeep would be more expensive for a SFH (or 2 in this case since I'd be living in one as well).The seller rented the 2nd house for $1200/mo but I'd add a washer/dryer and ask for $1300-$1450.

If they leave you before their lease is up keep their deposit to cover your one month of vacancy and move on  and this time add this to your  tenant screening procedure:  let the applicants rack up before you make a decision on your next tenant. 

With the poor tenant placements, lack of property upkeep, damage from not having pipes winterized, failing to evict nonpaying tenants, and a stellar occupancy average of 56%... the property management has costed me tens of thousands of dollars, if not a hundred thousand.

So in my operating agreement, I guess I wasn't distinguishing between ownership & equity vs voting rights and gave them the same weight.