I'm currently working with my RE agent and Lender who are trying to help me find properties and ask if I am interested in a duplex.

And worst case, they start to clean up, sort of clean up, just enough to stave off a few more months of actions but never enough to truly cure anything, and it's a cycle of pain for years. 

Your "generally cleanish" tenant will leave you a mess to clean up, you'll lose a couple months of rent and utilities, and you'll realize that a $50 late fee isn't extra income.Don't reward her with cash for keys.

The issue I find is that when I go to list my units, which are clean and moderately upgraded apartments in Little Havana and Allapattah I literally have 70 applicants in 24hrs via facebook marketplace or through the apartment rental platform my property management software interfaces with (like Apartments.com etc).So when I have 70 people lining up with first, last and deposit with no other middleman or agency impeding the process or requiring inspections or causing delays or requesting additional paperwork be filled out where is my incentive to go the section 8 route?

Consulting with a local agent specializing in those types of deals would be highly beneficial for you.Don't hesitate to dig deeper! 

Trulia, Realtor.com are other good sites to check but the information will be very similar to what you're already finding.I'd recommend connecting with local investors, agents, wholesalers, etc.

Maybe some sort of "white glove" organization exists, but doubtful.Also, it would be better to split it up for sourcing issues, just like hiring trades instead of general contractors.For example, it took me two years to find my agent. 

My suggestion is to do your due diligence a bit more and understand all the #'s that go into the underwriting, and find a market that is known for cash flow, and then find an investor friendly agent in that market to help guide you further. 

We did not need help in deciding what our investment niche would be; we needed help in creating and implementing a tax strategy plan for a married couple composed of a high-income earner and a real estate agent and business owner.

It connects my airbnb and VRBO calendars, offers automated messaging, smart lock integration, cleaning calendar/reminders, and offers pretty good income reports.