The reason people seek for distress properties, so that they can acquire the property at a low price and renovate the house aka "value add" so that they can increase the property's value and create sweat equity, then pulling the money out or cash out we call out so that investors can liquidate their money and reinvest on the next project @Albert Bui @Carlos Valencia

We are looking to increase our rental portfolio.

Wis Dells is a prime location for STRs to be eventually banned or very highly regulated given the large resorts with deep pockets and a lot of influence. 

Eventually, Class A property values increased to the point that even increasing rents didn't allow them to cashflow upon purchase.So, the flood of new investors switched to buying Class B properties.

If we rent quickly, we may increase rent for the next lease!

So if you're looking to increase passive cashflow you're probably looking in the wrong place. 

For example, could this potentially be a cash boom opportunity within the adjacent areas such as Kenosha and Mount Pleasant where one could buy low, sell high within a relatively short amount of time through appreciation, or would the presence of Microsoft increase cash flow in those areas?

Usually with Section 8 you need to give them 60 days to approve a rent increase (this is at least how it is in Massachusetts with my tenants).

Tenants and investors in general don’t care for their buildings as much/well as residential owners  (who fights reserve increases and special assessments the hardest - investors).

There may not be a lot of equity in it in just 2-4 years as real estate isn't increasing in value as fast as in the past.If you want to build a rental portfolio, your unrentable condo isn't going to help.Buying a new primary, that you can eventually rent out, would be better for building your portfolio.A challenge will be finding a new, TEMPORARY home, for your family that will be a good rental when you move from the area.