To all those stress I had to go through during this process the only consoling factor is the judgment amount I got through the Justice of the Peace Court.

Based on your post, it's probably best for you to simply not invest in Cook County for your own peace of mind.Sure, any tenant could stop paying rent and that risk is never zero.

Like Drew, I run a PMC, and I can say that most of our clients either had a bad experience with self-management that was costly or frightening (evictions, crime, etc), or they just live out of state and want the peace of mind that knowing someone can physically be at their property within minutes provides.

So, here’s my question.. do you think you’d be more comfortable taking the DIY approach with strict guidelines, or might a property manager give you the peace of mind you need?

And, depending on where your properties are in Portland, the value might be near its peak—selling while they’re in top condition could be a smart move.Ultimately, it comes down to what will give you the most peace of mind and the most flexibility for the future.

Again, this is a factual action that will ensure that you remain in control of your property and that the other tenant has the peaceful use of the property that is a legal right.Fun, huh? 

Getting this cleaned up now would push my credit score over 800+ and eliminate nearly $3k per month in revolving debt payments and bring me quite a bit of peace.

Here’s my two cents:Paying off the condo might make sense if your main goal is to reduce risk and enjoy the peace of mind that comes with no mortgage.

As for vehicle vs RE, I agree this was a vehicle but the peace of mind was unrelated. 

Completing the setup will likely lead to smoother operations and peace of mind in the long run.