If you are taking out a conventional mortgage of any kind, you can't buy in the LLC as it does not have two years of tax returns.You are also asking if an entire state is good to buy multifamily, which means you are too soon in the process to even talk about buying.

There's a self-proclaimed Section 8 guru online who claims he hires random property managers through this website called Thumbtack.

This can complicate claims payments for the named insured/tenant. 

Investment product marketers who claim to be GPs, GPs who claim “ownership”, insurance salesman who claim to be “financial advisors”, people who attended an executive training program claiming to have an MBA, what ever happened to honesty?  

., property management companies aren’t legally required to carry general liability insurance, but it’s highly recommended for protection against bodily injury or property damage claims.

Is it worth filling a claim?

I’m in the 33% tax bracket through my real job and this could be a big difference in taxes owed if we sold the property?

And of course we're in agreement on consulting a tax pro.

Salaries, compensation, rent, taxes, utilities, fees, MLS, etc.The flat fee model is a recipe for disaster."

(The claim situation)How did the umbrella policy protect you?