I have a background in consumer lending in a nicer area of town - typical clientele are 750+ FICO with cumulative DTI (with new debt) of <35%...

For example, if an HOA establishes a rule regarding exterior paint covers, deed restriction enforcement would be with that HOA.It is important to be aware that liability for breaking a covenant rests with the titleholder to the property, even if that individual is not the one who technically engaged in the deed restriction violations.

Investments we are considering or at first glance are appealing to us:fix and flipSTR *we live in a year round resort town (this is appealing to me with my hospitality background)Owner Contracts vs. renting?

I am not familiar with Philly or the technical questions you pose.I am thinking of this from a purely investment aspect.  

Ask for details on how they vet tenants, including credit checks, background checks, and rental history verification.References and Reviews:Don’t just take their word for it.

I am under contract for a 5-plex which is technically a commercial property.

Since you have a background in software engineering maybe this could be a gap in the market you could fill. 

I then do the background check on the 1st completed one that meets the requirements and has no glaring red flags.

Once you go to 5 units, the property is technically considered commercial property to banks so you'd need to get a commercial loan. 

Since I am active duty Navy with a recruiting and personnel background, I decided to reach out to see if I could help out in some way.