Note I have no affiliation with them except I use them and they have provided me a great VA.

Though I have purchased some with a mix where 330+ days a year, people parked in the driveway and the street except when there were snow bans, but there was enough room to fit everyone in the driveway/parking lot, and that was a hassle to deal with some days. 

Structurally, the property is in pretty good shape EXCEPT one problem that I cannot properly assess: the plumbing will not hold pressure.

At one point I talked to my financially advisor and he said that it would be smart for me to open a HELOC on the property, but not draw from it, except in the case of emergencies.  

Therefore, your request for a Type 2 STR exceeded the maximum 12.5% blockface density and the only way that staff can approve this request is for the Board of Adjustment (BOA) to grant a Special Exception for the rental.Based on this information your STR permit has been cancelled.

@Ashly Frasso not many PMCs do this as it's a headache except on the right Class A properties!

The only exception is for on-site managers, like you'd find living in one unit of an apartment building and managing the building on behalf of the owner.

The best projects I've seen from my desk are folks who are doing hyper-targeted, well-researched deals that are generally in higher cost of living (there are exceptions) areas. 

With the exception of some small markets in the Southeast, places like Cleveland are the only major metro areas where a regular investor can find cash-flowing assets with a mix of appreciation. 

There might be a few exceptions like everywhere else but you might want to check Airdna and you're gonna be able to draw conclusions right away.