The 'relocation specialist' with the company says the family would need minimum 3 months, and the insurance company would be willing to pay significantly over my asking rent price (I'm asking for $2000/month and they will pay $2600.

Hi Forum,This is Michael, I work in Coldwell Banker UAE as an offplan specialist. 

So it may be costing you more than just putting some skin in the game and recouping it back on the refinance or sale. 

And even then, those really experienced folks are able to raise capital by hiring intermediaries (aka brokers) who are specialists at putting together the capital stack (equity/cash from the LP/investor + debt/lender + co-invest from the GP/developer). 

Should I call a GC, mold specialist, or plumber? 

I would talk to local credit units with military specialists to see if they have anything customizable for where you're at in the process.

Where each party has some skin in the game holds everyone accountable.

Some HOAs will limit the units that can be rented ...connect with a condo specialist  realtor and you should get a good idea of whats possible ...if you will need a loan - get pre approved ...loan pricing for a 2nd home is  similar to pricing for a rental property

That being said, there are a lot of ways to skin a cat.  

.- Have some skin in the game.