Still decently affordable. 

We hear from a lot of out of state investors that Milwaukee is a great place to invest in real estate due to its affordability and strong economic growth. 

Since your dad is a contractor with access to affordable labor, the renovation costs could be lower than average.

The draw is actually this coming Fri for 2026The market for STR seems saturated in popular/touristic regions, however, if you have a unique property and offer affordable pricing, you may get descent occupancy. 

High-end properties might require a white-glove approach with customized services, while more modest properties may prioritize affordability and efficient communication.

Quote from @Andrew Steffens: Sorry about your frustrating issue - Airbnb is not only guest friendly but most of the time they will be the one paying for damage so they are going to try to minimize you. 

Are you basing this solely on what you can afford, or what you intend to make on it, or your target sale price? 

Some are basically affordable housing and some are vacation type rentals.

@Brett Riemensniderwe don't know all the details, but as i said that's a very expensive way to buy property - if you can't afford a property without overleveraging then you might just have to save up more.

I saw many highly successful hard working people lose money to them as well as people who couldn't afford it.