I'm going off the understanding that you still need to spend 500+ hours in the business to achieve material participation (please correct me if I'm wrong). 

before you spend another PMCs time. 

Learn to control your spending and pay off debt.

Quote from @Nate Sanow: Yes I own two that are near 100 years old and I will tell you they are a pain in the you know what compared to all of my post WW2 properties especially post 1980… layouts are better in the last 50 years and energy efficiency is better and I can keep going… HOWEVER to reply to the other aspect of your question, I’ve found appreciation is better with older properties in areas of the path of progress.

Spending on expensive upgrades is not the answer to improve your tenant base in this type of area.Keep the homes habitable, clean, and safe. 

I took the next 5 months to tackle everything myself spending approximately 17k in supplies and tools + paying a plumber and roofer 4k total to fix those issues.

You're much better off spending that money on a conference like STR Wealth Con or something similar.

If your time is worth $500 an hour I would spend the 5k on 10 hours of searching for a free mentor.

That’s why the successful wholesalers and flippers I know spend $10,000 and more MONTHLY on marketing.  2.

I’ve handled almost every aspect of renovations myself—plumbing, tiling, painting, drywall, and general construction.