I know the two that I attend regularly are great resources for exactly these types of things.

Our first partners was a friend and someone that I 'talked investments with' on a regular basis and I knew he had a large protfolio and a good chunk invested in CDs with low returns.

DSCR are way higher than the regular rates, how would i even cash flow with one of these loans?

Where ever you are, find an agent that is an investor themselves in your local market and see many deals they regularly do related to house hacking or type of property you are interested in and that will give you at least a starting point. 

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.