Do they have sufficient reserves? 

If you do not have capital nor experience, but sufficient ambition, a path may be to find a successful investor in your area and see if you can trade labour/skills for the opportunity to be an understudy.

Being notary public should be sufficient if this is profitable activity, you can also use your real estate agent activity once you get your license. 

You invest under your own name and carry sufficient insurance.

Both small units have wall HVACs (Is that sufficient for heating/cooling?)

An HVAC system that provides sufficient air movement is your best bet, especially with a dehumidifier built in.

Second, be sure your home's value is sufficient to pay off both the first and second mortgages (which you eluded to in your original post).

I'm sure there are some who can find deals in this market, but i have yet to find any homes close to being able to cash flow sufficiently in the last 3 years after literally going through hundreds or maybe thousands of mls, zillow or other online house listings. 

It also sounds like your goals (multifamily) don't align with holding on to that property.Also, you don't need 32 units for professional property management - 1 unit is sufficient.

I can't imagine having to qualify for each subsequent future property with strictly my personal income, so what forms of information and data have been proven to be sufficient in the eyes of the lenders you guys have worked with?