I think buying is a solid choice as long as you make some good contacts while your hear, most importantly a good property manager but also try to find a good handyman for service calls, a good cleaner, good yard person, ect.  

Fully finished basement. 2 apartments have access to a backyard patio.  1 apartment has central air.

Should I just hold out until I have enough cash to buy a cleaner property that will attract decent tennants, or should I actually consider buying a $30K property in a horrible neighboorhood since I can buy now, and POTENTIALLY start cash flowing now?

We have found thru the last real estate downturn and recession the air b & b just like many others took a hit and just boiled down location  and amenities as to how much of a hit.

Cleaner, faster and simpler.

That on the road part will also work it's way into using my personal unit in the duplex as an Air BnB for extra cash flow as well (250 plus days a year of travel...)  

Title is much cleaner for you that way and you won't have a problem with title insurance.

Air BnB is quadruple the amount of active users and such a better platform.

The one tenant mentioned there are gaps for air flow, which they tried to correct on their own (prior to us owning). 

I'm looking for a basic cleaning service for a short term rental (air bnb) in Jacksonville, FL.