Additionally, the STR market is quite oversaturated right now as well

If they do not want to price it well then do not take the listing.

If there are lease violations, mention them-you not having a key to access the unit WITH proper notice or in case of emergency is one of them.I'd also tell the tenant that they are clearly not happy there, so finding a new place is in their best interest as well and as they have several months, they should have lots of options.

You likely only made a down payment of 3-20% ....but you still get to write it off on the full value across 27.5 years.So 400k/27.5 = 14,000 ish a year of a write off where during the year you didn't need to incur an actual expense, no cash outflow. 

Otherwise, seems like a great passive investment with long-term upside! 

Online platforms like Zillow, PropStream, and Auction.com are worth exploring, and don’t forget to check out local real estate groups for deals and partnerships.Since you’re in Racine, the Rental Property Association of Wisconsin and Milwaukee REIA are great resources for networking, finding contractors, and learning about funding opportunities.

Very helpful and  I think that what you are doing sounds  like a very good pet  policy. 

The hilly terrain is a main reason for this and you can't really see that on a map so knowing the areas is key.We have old housing stock as well so big things like plumbing and electrical can vary cost wise if they have or haven't been updated.

Renovation work throughout both apartments, gutted and refinished the basement as well as extensive work in the private backyard.

Is it a market like much of the country where prices might be 5-10% higher in April?