Most Homeowners Insurance policies require the house to be owner occupied. 

If you recommend anyone for each role, I’d appreciate it.

It requires a mailing address for the Airbnb, but I do not receive mail there. 

Most professionals will recommend a separate LLC for every $1 million in assets but I don't think that's necessary.

Your operation, which earns commissions from marketing and recommending investments, is not a club.

There are schools all over, including Wilmington for sure. https://dpr.delaware.gov/ has all the details on schools and requirements, typically the schooling can be done online and then the test is done in person at a testing center. 

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

DSCR does not require disclosures as they are not sold to fannie and freddie mac but many lenders include them as a courtesy.

While agreeing that it creates bias, can someone recommend another real estate site that includes the crime map layer as it is critical for evaluating a rental purchase, especially as an out-of-state investor?

I have some mid range and excellent VAs I am happy to recommend as well if anyone is in the market.