He's got expenses, which isn't broken down by line item.

Teaching a new note investor how to invest in notes is teaching them how to think about notes not what items are on a checklist.   

Expenses are fairly low on the house as I've kept up well over the years and have replaced many CAPEX items already.  

This will help keep your personal items away from anybody that might bring legal action against your company.  

There is also the option to donate them to a nonprofit and reap the tax benefits for your current business.  

For big items, like the HVAC, you may be able to work something out with the vendor, as @James Skelton and @Nicholas W. have suggested, so that is worth exploring.

You'll need to substantiate all of that with invoices/receipts and attach a statement of safe harbor election with your tax return and then you can fully expense those items the year placed in service. 

@Chris FarrugiaThe roof is a maintenance item, and is expected to be in good shape.  

This is basically to make sure capital items are covered.Also, remember that it is ultimately a lease.

When buying a property, there are a lot of items that can be deducted at tax time, like property taxes, HOAs, utilities (if you pay them), mortgage interest, and depreciation (based on 27.5 years).If my income puts me in the 28% tax bracket, and those deductible items listed above come out to $10,000 (easy number for math purposes), would I be able to collect an additional $2,800 from the IRS...and would it be smart to include this in your cash on cash ROI calculations for the year?