@Noah Wood great start!  

Insurance did require there being some electrical updating but it did not require us to remove all K&TWhile you do not necessarily need to remove Knob-n-Tube - some insurance companies will not underwrite it, others will require you have it inspected and certified by an electrician, and, it is in good repair and has not had circuits inappropriately extended and overloaded/overfused, will underwrite it (sometimes at a premium).   

I agree with JD that the wood floors likely just need a good cleaning and you could deduct cleaning costs from the deposit.

Interestly all three of em didn't like painted wood cabinets.

A $1mm umbrella will cover you for the most part and in a worse case scenario, you might have to cover something, but I don't know that I have ever heard of a judgment of six figures in a landlord case without gross negligence or actively doing something illegal where an umbrella policy wouldn't help you anyways.In 19 years and more than a dozen tenants and 2 evictions that went all the way to changing the locks with there stuff still in the unit, I have never been sued...knock on wood.

I know they come in different shapes and sizes, but how much of a premium (as a % of the total value of the house, or $ amount) would you say a finished private rooftop deck with a Chicago skyline view adds?

Two, because it's only 2 feet high, insurance companies consider it a kiddie pool so they don't charge you more premium as a result of it.

As an investor and realtor in the panhandle (Destin, 30A, Panama City Beach), I'm biased toward my local neck of the woods, but I know there's pro's and con's to it. 

Sure the HOA takes care of lost of things, but at a premium cost.

My day job includes financial oversight of school facilities remodeling so I know enough to not "pull it" but rather "cover it" (may choose a wood laminate) but I have a few questions I am having trouble getting answered;1) In schools we are required to create and maintain an Asbestos plan with includes the identification, containment and abatement processes for all of our buildings.