I am looking at a constructing a single family that would extend into the floodway (not Floodzone) of a studied stream.

I will be managing the property myself.

Is there an assumed percentage already embedded there for property management, CapEx and repairs?

There are also online portals from many property management softwares that allow people to pay online. 

(I also have experience as a sales manager and as a real estate agent, so I'm confident I can make the switch).

Eviction and early termination history are big, big warning and for many managers, an automatic no.

Maybe, you can aim for a property with less of a down-payment and little equity used, should be easily manageable with the both of you.

Hi Dock,First thing you do is find a great property manager to guide you & partner with. 

Anyone here manage STR for out of town owners in the Tallahassee area? 

From CSLB:This section defines what an owner-builder is and the laws surrounding the practice.An owner-builder is what the term indicates: a person owns the property and acts as their own general contractor on the job, and either does the work themselves or has employees (or subcontractors) working on the project.The work site must be their principal place of residence that they have occupied for 12 months prior to completion of the work.The homeowner cannot construct and then sell more than two structures during any three-year period.Getting a GC license and going Legit is pretty difficult.