It makes it super easy to automate messages, notify my cleaners, and keep track of the calendar!

Just get an amazing cleaner who you pay slightly more (but still way less than property mgmt) to "run" your STR from afar.

I should add that an agent who fits all of the above criteria I defined will ALSO have a vendor list of lenders, inspectors,  handymen, cleaners, flooring guys, furniture stores, etc., etc. so you can start building your team immediately.

If you have the capability to answer calls at any time of the day potentially and do not mind catering to guests, managing cleaners, and contacting contractors, self management is a fine option. 

Most of the cleaners in the area max out at 4 bedrooms. 

We do this in California.5 Bedroom 3 bath house rented by the room.We had a lot of issues at the beginning mostly centered around cleanliness of common areas (Bathroom, Kitchen, Living Room).We scheduled a biweekly cleaner and issues went down to near 0.Be very selective with your tenants get the place cleaned regularly and chances are it'll be fine.

I like your idea and maybe even go further and have a complete addendum for drains/sewers if you continue having these issues and the PM should discuss this at the walkthrough before the tenants move in instead of you having to pay the drain cleaners $500 for every unit you have.  

Was the Crystal Ball at the cleaners that week? 

Be proactive in your upkeep and repairs, don't wait for a complaint to address needed maintenance.This means if you remotely manage,  you or a professional should be checking the property above and beyond what the cleaners have to say.

Although an Airbnb here and there doesn't make much difference, the impact of those 50%+ Airbnb buildings is definitely negative- lockboxes on every railing, suitcases and confused travelers in the lobby, late night parties, cleaners constantly in and out, unauthorized persons entering and exiting the building...You've got a great idea - we own short term rentals in Seattle, Stevens Pass, and Alaska, and our ones in Seattle are EXTREMELY PROFITABLE.