That's a tough one.

All I can say is that you'll get a much bigger bang for your buck by claiming these expenses directly against your 1099 income on the Schedule C.

Plus, it's important to remember that the IRS is very "form over substance" oriented. So even with the expenses you paid during the first half of the year, if your total 1099 income exceeds your total expenses for the year, I think that the IRS would think everything seems to be okay with your tax reporting. And if your total expenses for the year don't exceed $5k, and you won't show a loss for the year, you'll complete the 3 line Schedule C-EZ instead of the more detailed Schedule C, lumping all of your professional expenses together on one line.

Finally, if, on the other hand, your expenses from the first part of the year would push your Schedule C to a loss, I would be more hesitant to report those expenses on a Schedule C.

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