If we did this, it wouldn’t make much sense to include my brother since he has not been involved but I would like to include him as we are planning on acquiring more properties in the future.

or do I need more like $3.0M for landlord liability?  

It felt like a huge risk because I wasn’t familiar with the area and wasn’t great at screening agents or property managers.

It sounds like you’ve done some good research already.

I would like to hear your thoughts when it comes to looking for insurance coverage.

With the luck of the market, I benefited and realized that real estate is what I would like to do long term.

Seems like Google doesn't partner with AirBnB like they do VRBO, booking.com, and others so that means my property won't show up as a vacation rental with the "check availability" booking link on google maps or google web search. 

The seller will naturally want the highest price possible, and their agent is likely to push that "potential" value hard.

Typically I have my painter come in a "touch up walls" like 300 bucks max.

Private investment in these projects seems like a challenge as I can't see how they'd get paid back on their principal.