My question is, would selling this asset now to clean up all my personal debt (~$50k) with the leftover used to reinvest be my best move currently in your opinion?

I know the issues with the building, the quality of the condo, and the state of the association.

.- The management company charges a management fee of 10% - 15% which can be a little higher than average property management companies, but that cost may be offset by higher quality of services.- The management company also charges for other services such as fee for coordinating maintenance and repairs, and turnover and releasing.

Everything time a property owner has turnover they have costs for releasing, vacancy, painting, cleaning, make ready, etc.

After waiting out a lengthy eviction and doing nothing more than a clean-out, we listed it with a realtor—and walked away with just shy of $200K in profits!

They have lost many employees and the level of service and quality has been dismal.

The City has done a lot of work to clean itself up in recent years so you will find not only a lot of rehabbed houses, but businesses and store front rehabs, too.

Hire a reliable co-host or property manager (15-25% of revenue), automate pricing and guest communication with tools like PriceLabs and Hospitable, and build a strong cleaning/maintenance team to handle turnovers and inspections.

As Josh mentioned, it's important to find your right fit, I wouldn't focus solely on price especially if you're looking to be very hands off and you're looking for quality. 

A hard money lender typically will go from one loan, to three, then three plus depending on quality of the flips and your liquidity.