Moving on was tough, but helping him make peace with that was main part of the negotiation process no one else touched on.

Hard to produce cash flow or break even with that much debt, at that rate.House-hackers, however enjoy certain one time (non-scalable) advantages that should be taken advantage of in the early days: - They can assume pre-existing debt like VA and FHA Loans (rather than take it on Subject-To which is dramatically riskier).- They can rent by the room and self-manage to produce day 1 cash flow.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

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?

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? 

For peace of mind, it's worth it, don't you agree?

Fireworks lit up the Strip from nine hotels, with over 400,000 attendees celebrating peacefully.

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.

Lake Berkley or Terra Verde come to mind, they are peaceful yet still fairly close to the parks.

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.

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.