You will also want to check in on your local laws about increases as well as compare them to Section 8's regulations. 

Maryland doesn't regulate PMs (which is a whole other story), however if the PM does have a real estate sales license (i.e., they're a Realtor) then they can be subject to discipline by the Maryland Real Estate Commission, and you can be compensated from the MREC Guarantee Fund.

It’s important to note that if an outside property owner approaches you for management services, you must be licensed as a broker to comply with regulations.

Practical? 

Usually, zoning regulations is for a certain area, and exceptions to it are only allowed after a zoning board meeting, and in my area, neighbors within 400 feet are invited.

Furthermore, maintaining rigorous property management practices, keeping thorough records, and implementing robust tenant screening procedures can also mitigate risks.

Are there specific reports or practices I should follow to ensure clarity and proper management of both types of accounting?

Short-term rentals are often regulated by the city and limited to certain areas.

Killington does a great job managing and working with STR owners and it's one of the places I always recommend my investor clients check out because of the STR-friendly regulations there.

You should check out Boston's short term rental regulations.