Many lenders hare restrictions or guide lines on how long you have to keep the house in order to flip the house, while others have guidelines on how small a mortgage they will consider.

I'm also looking for a PM for my property in cleveland heights!

Where can I find detailed zoning information (beyond just the code, such as max building height, maximum percentage for building size, etc.)?

And Worcester needs housing and leaders look kindly on seniors and any deed restricted housing. 

Quote from @Jeremy Greenamyre: If the goal is to incentivize housing construction, the federal, state, and local governments could also address the disincentives - environmental restrictions, "green" requirements, restrictive zoning, studies, etc.

Although HELOC'S are available on 2-4 unit investment property homes, reduced Max LTV's, rates and amortizations can make $250k+ equity lines even more restrictive. 

The ceiling height might not be high enough.  

There are STR zoning restrictions, you will want to research on those before jumping in. 

Does anyone have any suggestions for how to get around these restrictions, or know which if any municipalities don't have these kind of restrictions?

Some lenders will require secondary appraisals, or a desktop appraisal, will want to see some sort of improvement on the property, and may have cash out restrictions.