The condo itself was cheap compared to same-sized units in other places without board-ups, so I was willing to take a gamble if it wasn't for the potential insurance problem.

Seems like such a gamble to me but I really love the place.

Owner-occupied ratio no longer met, HOA being sued etc.So in essence it's a gamble anyway when hoping for a future sale process being smooth when talking about Condos.

It just makes no sense to have that approach bc to me it's more like the annoying spam calls I get daily asking me if I want to buy a warranty for my Ferrari even though I already have an extended warranty.

BTW I spent about 7 years working in Black Hawk and never lost at gambling.

I think @Brad Larsen also gave you some great advice about the benefits of a career in Property Management as well as advice on taking a gamble on yourself, the way he did. 

Since it seems like you need more money and less debt, I think the best way you can get to the "real estate gambling table" is to first get more money.  

What you are doing is gambling with your future.

For me it was a gamble to get the licensing, I was getting a divorce and didn't have extra cash - I put everything on a credit card.

The tenant originally stated he had gambling issues and today when he called he said he had money invested in the USA stock market which 'is taking a long time to clear' this seems like an unlikely story and another ploy to extend the eviction process.