This provides you the greatest leverage in negotiating because the seller should disclose the defects to any new buyer and knowing this they are more inclined to come around to the terms you are seeking. 

Also - if anyone has rental properties in this general vicinity who can provide insight / verify my assertion that its not a war-zone I’d appreciate it !

In my rental agreement (lawyer reviewed and approved) it specifically says no smoking or vaping within 20ft of the building and all butts must be left in a coffee can with sand in the bottom and one is already provided in the "smoking area".Explanations are given for allergies, health, and second hand smoke etc. etc.I've not had any issues yet.

It’s a way to “sneak” extra funds in to your retirement account.

The money I pay in rent for the extra time is offset as soon as I am in the quadplex for 16 months. 

Tampa and Orlando are both very strong demand and price, but provide some safety with appreciation and Florida overall being sought after.I can recommend an agent for you to utilize in Tampa or if you are interested in Orlando, let me know.

By providing wrap around financing we netted $412,000 cash plus equity of $673,000 in the “wrap”.

(assuming because that's what that price would most likely get you) How much extra cash would you recommend having on hand AFTER buying the duplex?

It's circumstantial and depends on the services and value the service provider brings to the table.

I would also throw in Facebook, and spring the extra money for the promotion.