Quickbooks can't cope with divvying up my new roof or my insurance and water bills 60/40 while also allocating 100% of my unit turn costs to Unit 2.

However at this phase of my business a huge out of pocket expense like replacing siding, roof and decking from a major storm would be enough to really hinder my growth for several years. 

The property was built in 1900 and we don't know how much useful life is left in things like the roof, foundation, HVAC, electrical, plumbing, etc. 

Here is an article that I found on the Veteran's United website because I am trying to do the same thing:https://www.veteransunited.com/valoans/va-rehab-loans/The article states:"Here's what you can do:Repair or add new windows, doors, or sidingRepair or add new roof or guttersInstall new HVAC systems or water heatersImprove insulationWeatherizeTreat mold, lead paint, or moldMake updates to improve energy efficiencyRepair or replace the flooringRepair or replace electrical or plumbing systemsAccessibility updatesIn general, the project has to improve the property's livability and value and must become a permanent part of the home."

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.