I bought some replacement gravel ($1,000) for my driveway. Can I deduct this?

Yes, it is an ordinary and necessary business expense. Since you use the driveway for personal purposes, apply your Time-Space Percentage to the cost and deduct it in one year as a repair/maintenance expense on IRS Form 8829 Expenses for Business Use of Your Home.

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One of my parents is constantly late picking up her child. I have a late pickup fee but I have a hard time collecting this. What can I do?

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Can I deduct the cost of plowing my driveway?