What's going on @David Hanson - If you have a degree in finance and real estate...and it sounds like you are a go-getter, then I highly suggest looking into some Chicago commercial real estate brokerages.Other options would be some larger property managers or developers.  

I am in land development on the east coast of Florida.

I think the biggest challenge with STRs is the initial setup and development of systems. 10-15 hours a week is more than enough time to manage your STR once you have all your systems in place (think cleaners, guest messages, house turnover, pricing management, etc).

Learn where that quality lies in quantity, then develop a road map to that location (or locations).  

I'm an agent and investor/developer in Los Angeles so I really understand this pretty well!

To summarize, I helped build a 110 unit building and the developer received incentive to have spectrum installed in their units.

The more deals you review, the faster you’ll develop pattern recognition.

You can con me into buying one deal, or you can develop trust with me and have a super-long-term relationship where we do many, many deals.

Still early though.Will definitely keep the thread updated on how it develops. 

I've developed a decent size buyers list over the years, as my local market is a really good market to be in and price of entry is very cheap.