Even part of East Cleveland.

My biggest conundrum now is I want to be my own GC because even when I play with smaller numbers they’re still out of reach for me to be able to attain this goal and afford the monthly mortgage with taxes and insurance.

And the cracks mostly follow the drywall seams from what I can see, which is typical....And as @Patricia Steiner said, it doesn't look like a pro installation....You could ask the Contr to use a flexible compound if this happens again, or maybe even now...https://www.dap.com/products-projects/product-categories/pat...Like everyone else said, I'd have it repaired - by a licensed Drywall Contr. - and then just check in on it.

Long-Term Rental Rules: Even though my properties are long-term rentals, are there any tax benefits I might be missing if I occasionally rent them short-term?

Even better if you buy 2-4 units, live in one and rent the rest - then repeat every 12 months.

Post Dodd Frank sellers have continued the same bad practice of selling houses to occupants with financing at selling prices that are way high, can't be justified via any type of 3rd party valuation (appraisal, zestimate, tax value, even recent sales in the same area).   

I always tell clients to take care of the hard job first - If this is a sellers market then find your property and even get it under contract before you sell your old property.  

My advice: don’t overthink it—your first house hack is about learning, so pick a strong rental market, ensure solid demand, and lock in a deal that gets you close to break-even or better.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

It all evens out.