I don’t understand how this isn’t a clear-cut case.

Best way to understand this is research appraisal standards and means. 

I don't know the Baltimore market but have a friend who is a very savvy investor there and maybe he would do some coaching to help you understand which way is up.

This will help you understand your options and decide if it's the right time to hire a pro. 

This is something I aim to understand more about.

Their program is simple to understand for the most part.

Whichever direction you go, be sure to work with folks who understand this and gives you the confidence to take reasonable action - I'd personally take an okay investment and weather the storm for a few years that will eventually perform well, and do that each year - rather than take 3 years to wait for the best deal possible.

This is correct, so I would disclose every aspect of the sub to and how it relates to the seller, perhaps going so far as to insisting the seller sign off on an acknowledgment that he understands the ramifications.  

Instead of 40 houses cash flowing $200 each or $8000/month, you buy 10 houses and pay them off for a cash flow of $10,000/month with 1/4th the headache.People don't understand the amount of time, energy, and stress involved with managing a lot of doors, especially if they are lower-class properties typically needed to generate cash flow.

But consulting with the town would be good to try to understand what they're permitting process is like.