The other benefit of doing it myself is that it's forced me to be much more involved and to better understand the finances of my investing business.

The property is equipped with modern amenities including forced air heating and central air conditioning, ensuring year-round comfort for tenants.

If my buyers walk then I will be forced to sue them for any monetary damages that will cause as well.

Could I be stunting my growth as a person by not changing my environment and forcing myself to adapt? 

If not you may have to legally force the sale.

It's taught me patience, and has forced me to think conservatively.

This allows you to buy into a great neighborhood at a substantial discount, as the stigma of Youngstown will force a discount on all properties in it.

If the economy slows down further and unemployment begins to rise, I believe that their hand will be forced to an extent and the FED will need to put some attention on those figures.

Buy the rock solid rental and get your appreciation, cash flow, depreciation, principal pay down, equity capture on a discounted by and forced appreciation gain for a well targeted rehab.  

IT Business:With $250k in cash savings and significant untapped equity in your rentals, you’re in a strong position to leverage your existing real estate knowledge to grow your portfolio further.The real estate market, particularly with your ability to do your own rehabs, might provide you with more immediate and scalable opportunities for wealth building, especially if you can find properties that need work and force appreciation through value-add strategies.Balancing Both:You don’t necessarily have to give up the IT business entirely.