Wichita seems like its a strong market.

I’m not looking to be an active/public realtor, just need a place to hold my license.For context, I currently hold an active HI real estate license in good standing and have strong networks on both Molokai and Maui.

For example, areas like Chicago have a strong demand for furnsihed rentals, especially in neighborhoods near medical centers.

The fact that your property is in a strong area with high-quality renters and growth potential is a major advantage.First, revisit your numbers to include all expenses and potential tax benefits, like depreciation and mortgage interest deductions.

If you don't have anyone that has booked a week or so before, you can move it to 1-night min on weekends but I would hold strong personally.

As Milwaukee is my home market I have a strong interest in investing here.

Sounds like you have thought out a lot of this, but maybe also hold a competition with a cash prize at your closest architectural and design school.Can you build it cheaper than someone like this?  

What are your returns like, is it a strong STR market?

All the markets you mentioned are solid choices for affordability and long-term growth potential.If you’re looking to narrow it down, consider Indianapolis or Columbia, SC, as both have strong rental demand, landlord-friendly laws, and stable economies.

Still strong but lots of competition, so you need to research what works: good pics, seasonal pricing, amenities, etc.