You add up all your itemized deductions.

(FYI, not sure the timeframe you're doing the analysis on but most of these major items I'd say have replacement times longer than most investor's timeline horizon for holding the asset... still)Roof: 15 yearsWater Heater: 8-12 yearsAppliances: 10-15 yearsDriveway: 25-40 yearsFlooring: 10-25 yearsPlumbing: 25-50 years (copper and PEX), but Cast-iron plumbing likely already at the end of its life in 2025 if it was installedWindows: 20-40 yearsPaint: Interior - 5-10 years.

The rehab estimate is itemized to a certain extent. 

I personally think it's a delicate balance and depends on where you're starting from.

There is a definitely delicate balance between the 2

Outside of donations and property taxes, you don't really have control over timing of your itemized deductions.

I only have lists of essentials in relation to kitchen/bath items (so clients don't forget to buy a toaster, collander, etc). 

More importantly, I walked away with several actionable items that I can take in this next week to improve my business. 

My point is that a lot of the expensive items have long lifespans, but they still have lifespans.if you want the best estimate, fill out a spreadsheet with lifespan and current replacement costs on all items and calculate out a sustained maintenance/cap ex costs.  

If you offer a free-will donation to the church, that could potentially be a charitable deduction if you itemize, but not a business expense.