The stock market is up something like 80% of the days long term.

Quote from @Greg Gallucci: I'm starting to look into the Huntsville market.

It's a small place so I'd guess it won't rent for enough to cover your expenses anyway so I'd probably sell, especially if the loss is small, it unless it's in a great neighborhood that you think will do well over time. 

The job market is tight here in Lake County right now.

I am now looking to enter the Chicago market, I have heard good things about that market.

STR-friendly markets make it easier to get started and grow your business, and the lack of state income tax is a huge perk.

There are many markets that this will work great. 

One year after I used that property to pull a HELOC and this year used that money to purchase an off market 4 family property in Clinton for well under market value, which I just recently finished all of the repairs and upgrades on.

We’ve seen this issue cause otherwise wonderful new builds to sit on the market because it just doesn’t work with peoples furniture. 

Ideally I wanted to live in Lake View as that's my dream neighborhood, but I just didn't have the funds/income.