So, basically it sounds like the most critical piece of info to have when purchasing would be that the zoning cert matches the units you have. 

Just report top line and match it to their sales tax returns.

The lender will have policy limits and deductable that they require, a Loss Payee clause with loan number, and it needs to match whatever type the subject property is... meaning if you are occupying one unit of a multi unit.

How in general, does RE investor keep borrowing/leveraging in order to grow their portfolio where assets and liabilities are matched so to speak.

I don't know how much crossover interest there is between RE on BP and crypto but there's an enormous amount of innovation happening in cryptocurrency finance that could be a great match for RE investing. 

Is he allowed to play with matches - who let this guy out?!!!

I know it’s not the best job for connecting with other people but it provides a stable salary that with time will allow you to get mortgages and most full time positions come with full benefits including insurances and some type of retirement account with many employers offering a matching benefit.

If we could match it he would've gone with us because he likes us more.

@Sheena DrakeWe take pictures of the receipts and match them up to the corresponding expense(s) in our property management software (Stessa).

Otherwise there will be a problem lining up an insurance policy with a loan vehicle - they have to "match" or the lender won't endorse.