I'm struggling to find ordinances surrounding the requirements and regulations with this strategy in Cleveland heights.

Quote from @Fred Bagirov: I am new to Cleveland and trying to understand the market, rules, regulations (and loopholes, if any) with STR properties. 

Specifically, does the regulation still apply if I am the host and reside adjacent to the rental property?

If you get serious about a particular unit ask to see the associations bylaws/rules/and regulations.

I had 2 STRs during Covid and they were both slammed with people wanting to get out of the big cities with the hordes of people, and away from all the mask regulations, restaurant closures and all that.

If you’re looking for information on zoning, regulations and permits, I would start with one of them.  

I have practiced real estate and this is my third personal investment so I am more savvy than most, some people really would get screwed out of a good deal in a process like this for no good reason.

Here are some practical strategies to help you navigate the process.Start by understanding the local real estate market.

The book provides practical advice and insights, making it a great starting point for beginners.

Myself and family truly loved the property and house; just want others opinions on if this may be a mistake to proceed, or does this appear common practice for the age and location (upstate New York).