I know the current local bank I am dealing with I had to share my resume for them to for them to evaluate if I have the experience to handle the vision I shared.... is working with a commercial banker a good idea as well?

We have helped clients through the maze by evaluating their PM software and accounting needs and help them make the next step decision.

Read Brandon Turner's book on investing, he has a great section on evaluating properties that a lot of folks use for their baseline.

Ignorance, or they don't know what to ask for or how to evaluate it, fear of looking foolish?  

2) Are there any recommended sources or books for learning how to evaluate the condition of property or methods you would recommend I consider? 

In stead of fix n flip they fix n rent n evaluate. 

I'll evaluate where my money gets me more benefits.

However, I’d get your property re-evaluated before putting it on the market.

The owner may be required to provide a structural engineers evaluation prior to warranty work.10.

I currently own some SFH in Orlando and Jacksonville but in the process of evaluating MF in central FL (Lakeland, Orlando, Jacksonville and Tampa.