I BELIEVE it can be a win-win, but if approached incorrectly it can very easily come off as "Hey, you're out there hustling and I just want to ride your coattails".Any input is greatly appreciated.

A bike ride, bad golf or home with a movie or to the river with my dogs.  

Just ride it out because you will need to repaint regardless of if the move out tomorrow or 10 years from now. 10yr is better.

You want to make sure that your underwriting is conservative enough such that you can ride through the adverse cycle and sell at the next market cycle peak.This means factoring in a higher than market vacancy rate. 

(And we also want to ride all of the big roller coasters of the world!)  

Real estate is a roller coaster and right now this ride is near the top which means profit margins are thin.

Well first of all I want to apologize in advance because I've probably called you since I see you're in Miami Beach.You just gotta ride the wave to be honest.

You would still need to do all of the hands on due diligence you describe, and if you talk with the provider they may perhaps let you "ride shotgun" on the deal to learn as you invest.

@Tim Roberts I can send you some examples of multistate portfolios I have done for investors in the last few months.I think you will find there are very competitive insurance programs for the CA properties, but they are only available for CA properties.IL & CO are a little easier to combine onto 1 policy while keeping the premium competative, but the hail and wind issues in CO may make sense to break them out again into separate policies.

I have a property in Kellar and the property management company informed me that a hail storm had damaged the roof.