He and his wife are regulars across the tech podcast/news spectrum.  

Also, regular maintenance inspections can do the same.

With 5 days already that's a super flexible cancelation policy (even if Airbnb calls it "moderate") and I doubt you'd re-book that close.But yea, my confusion still remains what the heck these guests are doing that they're regularly unable to travel for an entire 3-day span. 

The downside here being the unit is on a busy two-way road, close to two major junctions where commuters regularly drive through on their way to manhattan.Assuming the most conservative rental numbers and the worst-case capex expenses, I'd be at a 5% cap rate and a negative cash flow of around $ - 500/month at this price.

Many of them regularly help investors purchase properties that they plan to rent out as a STR, and then follow up with a list of their recommended vendors to get their listing set up.

If she travels regularly, she may not meet the definition of "agent" because she's not "readily available" to handle problems.

Long-distance Landlords typically let properties deteriorate or allow bad tenants to damage a community.A good PM watches your property, inspects the interior regularly, choose solid renters, removes bad renters quickly and efficiently, reduces vacancy, handles maintenance quickly, keeps your property at market rates, stays current on the laws, and much more.

I shop insurance regularly but can't beat coverage or rate at Farmers Insurance.

Say if we were to treat it just like a regular partnership between to non lovey dovie individuals, how would an agreement like that be structured?  

If you do not build record keeping then consider regular audits on your management company and add a clause in the agreement that requires this.