Quote from @Jared Hottle:
Midwest markets scare me a bit as they are not destination type places to stay. However that being said I had a similar experience in Omaha when I travelled there for a weekend. Seems like demand was high and supply was low. Price seemed high for what we got so maybe there is something there. Also, those midtier markets may not be bad as likely the zoning and use ordinances have probably not expanded to address short-term rentals.
I may be biased because I was stationed in Omaha for five years but I loved that downtown area. You have the following major events most people don't think about:
1. Annual Berkshire Hathaway Share Holders Meeting
2. College World Series
3. Major Concert Venue at the Downtown Center
4. Major Hub for business conferences due to its central location in the midwest
5. The downtown area is going through a revitalization aka gentrification in North Omaha that was known for high crime low income
6. Midtown area is expanding as well with big outdoor events like Octoberfest
7. Creighton University basketball is a big attraction downtown
Those are just some of the things that made Omaha so much fun and there was always something to do between spring to fall. I will admit during the winter its pretty slow but there are still concerts with big headliners attracting people from other nearby metro areas and states. The only other place I can think of thats close to offering what Omaha has is the Power and Light district in Kansas City Missouri.