If the carpet gets torn up you can put in hardwoods but I'd use the 3K to make the STR stand out in other ways

Can't stand them.

Not sure how it stands now. 

Are all tenants in good standing on the rent. 

I have had several Colorado LLCs (single member LLCS with one single family residential rental per LLC, so very small-time) for a decade, and always file my periodic report so am in good standing with the Colorado Secretary of State, but have only just heard that I need to file a BOI report before the end of the year.

You are immediately standing out from the crowd, this is  a good thing, those people dislike their jobs and choose to not do anything about it.

The 19122, 19123 & 19125 zip codes stand out as neighborhoods currently experiencing this issue.

$200/mo has been the long-standing average in Milwaukee, but with current rates you'll need to bring a bit more down payment.However, stay above at or above median price. 100k does buy you a lot of headaches and future capex.

I cannot think of a way that you (the LL who stands to "benefit" by them repairing their own space that they are paying you to use) will come across in a positive way.Plus, the tenant who incurred damage due to the other tenant's leak, may have some legal rights to have the tenant with the leaking pipes pay for the repair in both spaces.Now, beyond the legal side, you also need cognizant that most mom and pop tenants (which I assume these are) are not great with their money.  

Take the time to craft a listing that stands out and is ready to book quickly once it’s live.