Roofing, piping, electricity, plumbing, and the foundation should be your main points of focus in a home as old as this along with what you mentioned. 

He has 9 houses all in poor condition, all occupied by people with low income scrambling to keep a roof over their heads. 

There's no need to continue saving because my roof could blow off tomorrow and I can write a check for it without batting an eye.

Are there any yearly updates required for the roof due to hurricanes?

This will hit me heavy on the front end because now I will essentially be out another 10K, which is certainly more than I was anticipating, and we're trying to figure out how to make that all work and keep our own roof over our head.

Same with a roof, plumbing, etc.

I have plans to get a free and clear property under control in capitol hill with an 8 to 12 month purchase option (because they're not ready to move out and sell just yet) then put a rehab VA conventional loan to cover repairs and upgrades, then air B&Bit (other than the roof, the home has all original everything so I'm not quite sure how to estimate needed repairs) Now because of this rule I can't.

Rent:1200Unit 3: 4 bed, 2 bath Rent:1200Existing conditions: has a 2 car garage, in need of major repairs ie. new roof/garage doors.

How about roof, windows, siding, etc? 

In the other there was some roof damage but based on what they would cover it didn't make sense to go forward given the deductible.