I have seen it happen maybe 5 times over the years and directly involved in 2  .. the one I mentioned that I bought the first after the second was bought and another were I was bidding but got out bid B/C other bidder did not know about the first.In the its a Small World category..

As others have mentioned, the virtual accounts you can set up for each property was really intriguing to me. 

Steadily is my go to, but I see you mentioned them already. 

The traditional carriers you mentioned are not good options in this space.  

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. 

Quote from @Mitch Holmes: I would flip as well, as Chris mentioned.

The person who gave me a demonstration mentioned that by using it, listings were much better ranked on Airbnb (he emphasized that the listing updates every night, which is good for the algorithm).

That to me is the simplest deal structure and the least "risk to you" as you aren't waiting for the final home to complete to be paid, as I understand it most construction loans close on the "dirt" up front....although like everything in real estate its infinitely negotiable and changeable.  

So I waited a couple months, and they reduced the price.

Given that the industrial market is softer than the prior few years, I intend to buyout/wait until current leases expire and leverage the space into self-storage.