For example where does water drain on the property.

If you are in too low lying of an area, it may not be the wisest long-term play (unless we start building dwellings under water!)

I wouldn't limit it to roof as wind and water can damage other areas of the home..what if a window was left open and the interior now has water damage etc...Did you already bind your insurance (likely not if you are two weeks out) So there may not be a reason for them to dictate you get it reinspected. 

There is significant water damage in the kitchen and also mold (possibly from over time, but not sure).

Though, there is no real checklist on what they are looking for or what the standards are.

Thank you  You can do a standard cash out refinance and wait 3 months once the rehab is completed.

I'd just run your numbers on the new development i.e. how much can you get land for, building permits, water/sewer hook-ups, etc. 

The problem is that there constantly seems to be fees being charged to me an example of this is in the contract  there is an additional 100 dollars allocated to sewer and water that the tenant automatically pays every month with rent and anything outside of it should be billed to the customer (there is no specificed time when this will occur on the contract) but it appears to be billed to me and after speaking to IIP it's like they made up rule on the spot stating that after 6 months all of the additional utility fees would be billed to the customer and in the meantime I am being charged for it.

Commercial space rent in the area for similar properties is $3000-$4000/mo but property taxes annually are $25k+, insurance $6k+ and other expenses such as trash, water, heat & electric, etc. 

Market and economy added value while I maintained the residence to high standards.