Ideally the owner would handle everything and would have no need for a property management company with only this single duplex in their portfolio. 

We are now appealing a denied claim with the insurance company.

You might try corporate housing by owner, or try getting in contact with some insurance companies for replacement housing, or traveling work-crews, etc. 

I would get an attorney or title company involved to create your loan documents to ensure they comply with the law and cover all the aspects you need.Another method that is likely your best bet to take on investors is to create a joint venture (JV).

My retirement system doesn't allow for me to roll anything over given that I'm still employed with the company and also under 59.5 years old.

I've worked for Superstar Car Wash, Circle K, and The Carioca Company. 

Does the operational company already exist and have income history?

Anything beyond that is going to take some blocking and tackling (reaching out directly to local companies like solar farms, construction, medical staffing agencies, etc.).

Typically, if you have a mortgage, the mortgage company will collect taxes and insurance when you pay,  so there is not really any budgeting required for this.

Suncoast is a very big company.