Central A/C is damaged beyond repair and needed to be replaced, which can't be done economically or with coopperation of the HOA and other neiighboring owners.

Your financial background is a huge asset, and it’s great that you’re starting locally in Milwaukee while keeping an eye on future expansion.If you’re looking to connect with like-minded investors, the Rental Property Association of Wisconsin is a fantastic resource for networking with rental portfolio owners, accessing legal resources, and finding contractors. https://www.aasew.org/For mentors, funding sources, and flippers, the Milwaukee REIA is another great group to explore. https://www.milwaukeereia.com/I’m a member of both and find unique value in each—maybe we’ll cross paths at a future meeting!

You still couldn't transfer the accounts from AirBNB and VRBO to the new owner.

If you don't have the most amount of liquidity and want to scale with as little capital as possible, I would focus on cash flow. 

With the exception of building a trailer on the property (these are hard to finance), this sounds like a good plan AND if you are using it for your business AND your business pays more than 50% of the rent (if you have more than 1 tenant), then this is a more financeable property in the eyes of banks and credit unions as it would be consider a commercial "owner-occupied" property. 

Fractional TICs give owners the financial independence that has been associated with condos, without the need to wait for a condo conversion, a process which can take anywhere from 2 to 10 years depending on the specific requirements for the subject property.

I purchased an STR a little over a year ago and my goal is to make it the best STR in our area before I even consider purchasing a 2nd STR.

Summary;  95% of all pre forclosure owners refuse to even talk about selling inspite of the empending auction. 

Look for a PM is also an investor/owner in your market. 

Or just any suggestions for the best bang for your buck areas that offer at least a little cash flow and appreciation ?