I'll head into the zoning office tomorrow, probably better than attempting get my specific questions answered over the phone.  

There is almost zero chance that you bring this issue to a head and they sign a lease with a good future prospect for the tenancy.

This is something that will be hard to judge at first but once you start getting the hang of walking a property, and doing the flips you will be able to estimate off the top of your head when you walk into a place.

I thought it would be extremely formal guys with briefcases and way over my head. i felt it rapidly grew my network, knowledge basis, and confidence that has propelled me to be successful in acquiring 300+ units over the last 4 years. 

@Nathan Gesner hit it on the head here.

Increasingly I have been given fake past landlords that can’t answer that simple question.It sounds daunting, but it’s really not that big of a deal once you wrap your head around it.

@Heidi Fahringer wasted time doing several calls and then a meeting with a CPA and then got shocked with their proposed fee.After even more wasted time trying to find out from them why the fee was 10x what I had been paying - a lightbulb in my head finally lit up and I asked the revealing question and found they had a minimum charge.Obviously, we were not a fit.

This can help with limiting the time your unit sits vacant.These situations can get tricky, but I always recommend staying level headed during your interactions with the tenant.The worst case scenario is the tenant ends up unhappy that you don't want them to break the lease early and/or they don't want to pay for an early lease break (hopefully defined in your lease agreement with them) and ends up damaging your property, costing more, prior to their actual move out date.

Some will succeed at having a roof over their head.

Maybe if you really like these guys and their work...and feel that they honestly got in over their heads, you could throw them an extra $500 just to appear 'nice'.