Subsequently we started a Reg D passive investment fund which allowed us to expand further and bring on a more direct structure to allow accredited investors to invest directly into the homes that we own and operate. 

Owen what you are saying is if a storm caused extensive damage to not only the roof but other parts of the structure as well, that damage may still exceed the high deductible, so it may still be worth the additional premium.

Now my lender are debating if I have to rebuild the structure completely with the insurance money.

So it depends on the structure of the LLC etc. , what it was formed to do,who owns the property, check with your lawyer if you are concerned.

To what extent you tell them how you structured the deal, bought the property or anything personal for that matter is up to you.  

The other states we do business in have completely different structures. 

These lenders may have more relaxed requirements regarding the ownership structure (LLC vs. personal names).Seller Financing: If the seller is motivated or willing, you could negotiate seller financing where the seller acts as the lender.

Plain and simple, there are just better markets for cash flow with less archaic tax structures and market swings. 

It's around 4 acres of land that could be developed into a cul de sac with ~10 SF homes.However the lot currently hosts a 5k sqft commercial/industrial structure (made out of metal). 

Here's how you can structure it:Contingency Clause: Include a clause in your offer that states the purchase is contingent upon securing a lease agreement with a tenant within a specified period.Time Frame: Define the time period within which you need to find a tenant.