All that being said, it might not be worth the cost of putting in parking, just be aware on the front end that you’re reducing your end buyer/rental pool by not having it. 

I wasn’t looking to add value or find something off-market because the time and effort just didn’t seem worth it compared to focusing on my career.

If so, you will need to apply for a change of number of bedrooms on the standard CHA rent increase form.

Just like most places, there are a few warzones in Springfield (not terrible, but I also wouldn't walk around there at night) that probably aren't going to be worth your time or money. 

Is it worth actually evicting though?!?

You already have a pretty solid portfolio, so adding another property and generating more cash flow might accelerate your wealth in a way that the Roth can’t match, especially if you’re planning to transition to real estate full-time soon.The long-term game for you seems to be building that cash flow and equity in real estate, and it sounds like taking the hit on the Roth 401(k) could be worth it for the immediate returns.

The end product will be great, as others have mentioned perhaps in other threads, Delta has not increased any of the cost, so there is still a huge equity upside.

Any underrated markets worth exploring?

All together around 80k worth of money invested.

If you pay off a property or owe more than it’s worth, you can still owe or not owe capital gains tax.