I think what you circled in red is not separation but just the picture.

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??

This is a great resource for everyone just starting out as well as seasoned investors.I would recommend calling and talking to all kinds of different players in your area. 

That the established players have the old way and it works well for them given they have already built a network of investors.That new operators, who used to have to use the 'old way', will migrate to the crowdfunding model (SEC definition)?

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. 

Here are just a few of the players you will need on your team.

You should build a stress test questionnaire that asks dozens of questions and requires the input from all team players.

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.