Ordinary vs Long Term sounds snafu'd - - get a CPA, not just some accountant nor bookkeeper. 

All the details of rent collection, leasing, maintenance, repairs and bookkeeping are handled by national class, professional property managers.

First thing I'm going to say is that their bookkeeper sucks. 

I don't have a ton of experience, although I have managed our 2 units for a year and a half now, handling leases, bookkeeping, open houses, etc. 

the safe harbor applies to amounts paid during the tax year to acquire or produce what the regs call a “unit of property” (UOP), you must meet these requirements: (1)you need to have written accounting procedures treating as an expense for non-tax purposes amounts paid for property costing less than a specified dollar amount (which will be 2500 for you), or with an economic useful life of 12 months or less;.(2) the taxpayer treats the amount paid for the property as an expense on its books and records in accordance with its accounting procedures. ( do this on your bookkeeping software or whatever you utilize)(3) the amount paid for the UOP doesn't exceed $2,500. as substantiated by the invoiceNote: The cost for the Unit of Property includes l additional costs (for example, delivery fees, installation services, or similar costs) if these additional costs are included on the same invoice with the property. 2) Small taxpayer safe harbor: To be eligible for the safe harbor, the total amount of improvements for the property for the tax year may not exceed the lesser of $10,000 or  2% of the property's unadjusted basis. 

Especially if you keep a bookkeeping system where all expenses, including this one, are recorded.That said, if you do have to prove this expense to the IRS, you have to prove two parts.1.

I tried to cheap out on managing my own properties, my own book keeping..

These are good scores, great in my book. Keep

For each line item, use a cost code as well so you can track how much you are spending from project to project and make the book keeper's life a little easier.BANKIf you are using a construction lender which is likely, make sure you get permission from the bank that it is ok to do grading and demolition before the loan is originated. 

I found a QB bookkeeper that was instrumental in helping me get it set up correctly.