I would suggest trying someone local, may hosts have find their last resort at a local insurance company.

One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions. 

You can find plenty of markets where nobody builds and you won't get competition but you won't get bookings either because there's no demand.It has been proven that, with short term rentals, it's the really professional hosts that make the bulk of the money (think the 80 - 20) rule.

Quote from @David Edwards: PadSplit host in Houston here, my experience has been good thus far.

If someone wants to host MTR, STR, whatever, they should start their own management company, not try to use this model where they can make additional money off of an owner if a property performs well.

A while back I was listening to an older episode of the Bigger Pockets podcast back Michael Greene was still hosting and they talked to an insurance expert. 

It's an hour and 35 minutes and the host's first language is not English - he's Hawaiian.

They record to the cloud and have many features.

The host is based out of Boston!

There is options for hosted showings via others.