After I learnt what I had to by making mistakes, hosting open houses, and closing a few deals - I switched to another brokerage that dealt mainly with offmarket properties and investors (both residential and commercial). 

The one you can scale.I know successful business owners in the fitness industry, tanning salons, real estate, window coverings, maintenance, billboard, ATMs, etc.Generally, I would be skeptical of jumping into a business based on YouTube videos hosted by and featuring people that are likely primarily trying to sell you their respective courses.Small businesses can indeed be great investments, but they are hard.  

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. 

., Event Venues): Purchasing a property like a ranch for hosting events is possible

We host an investor meet up every month in Alexandria, VA.  

She is an investor-friendly agent, investor, and STR host.

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. 

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.

Just wanted to add the MidAtlantic Summit convention @Dave Van Horn and his team hosted last year was top notch with the next one planned for October 2019.