Given the historic preserve nature, I can foresee rehabbing these older homes with a ton of red tape associated with it.

Is it a red flag that I almost immediately got a response??

Airbnb estimates ~1600/mo average, and I think it is a bit conservative given the location next to public transportation, "coolness" of the unit (100+ year old building that will stage and photograph well), and relatively underwhelming alternative Airbnb and hotel options.Furnishing everything is my biggest unknown that I'm working on, but I would greatly appreciate hearing about any red flags/concerns/oversights that jumped out at you while reading this.

Consider the following: First, if you are buying the home with first time home buyer's  loan programs, you will need regular owner occupied insurance to start out with to ovoid any red flags. 

But the business credit would probably use your personal credit to start, so there may be a bunch of inquiries that could raise some red flags. 

In my area the meters have little red triangle objects inside the glass covered meter gauge. 

If they're good, they'll usually give you a rough idea of extensiveness of the repairs, or note any bright red flags.

So things that are a red flag for me may be fine for someone more aggressive.

How do you seasoned investors find good deals on rental properties, and what are big red flags that scare you away from certain properties?

It gives us an uphill climb that is completely unnecessary.The worst part of this Zestimate scam is that they show you the Zestimate in big bold numbers, but you have to dig deep to find the chart I posted here.