Request a quick phone call consult and she'll tell you what you can expect to pay to build the utility workshop and if she thinks you could build a shed/apartment. 

I'd just weigh your expected returns in the market vs your mortgage interest rate.I've actually been tapping the HELOC equity to re-invest into the market which is an aggressive play but if I can beat the interest rate (3.75%), I'll be turning a profit by doing so.

All units are occupied which the leases are expected to end within the next two months. 

In the next year or so, we expect to sell off two SFR's and a duplex in Independence, MO to 1031 exchange into another smaller multifamily. 

Therefore, it is a fair expectation that you ask the seller.

I would say no because 1) she doesn't report her income (not a good sign) and 2) if you feel a larger deposit or extra prepaid rent above what you would normally require, it would seem that you are already expecting her to be a liability - which usually, they will be. 

That said, if you keep your foot in their *** 24/7 then they will have a different incentive ;) EXPECT WHAT YOU ACCEPT when you don't get an answer back for 7 days, you must make it painful for them.

I expect every small bank has their own particular policies, but I doubt many require you to refinance multiple properties.

Wife and I are expecting our first in August, sooo I know nothing lol

It will give you a heads up on what to expect.