After some time I approached him to see if he would consider an offer (my wife and i have wanted to get a rental property or two for some time.) 

Hire a real estate attorney early in the process who can assist in navigation and help provide contacts.This is just one way to approach it but it's how I would.Best of luck!

Can anyone share their experience with this approach?

I think we are leaning towards "the hands off" approach due to the fact the property is already established on AirBnb with the superhosts. 

Safe, smart approach for the new kid on the block.Also, accept the idea that you needn't only invest in your local market. 

However if the clog was found in the main of a particular unit before it joints the main to the street. then by all means approach that tenant with a bill, Hopefully you took some pics of the stuff that you took out so you can prove your case.

My friend asked who the guy was as he was on the phone when we approached.

Nobody ever approaches us for a loan and says" I need a loan and I'm going to fail to pay you back," when in fact that is how we look at every loan request.

Better option there is door knocking and creating a systematic attach and approach.  

Either way, set your goals and approach the meeting with that in mind.