To my knowledge, you are not allowed to claim educator expenses as a business deduction.
I never itemize the $250, but I do keep the receipts. I claim it on line 23 form 1040.
Also, I write checks when I purchase items for fundraisers and claim them as a charitable deduction. I rarely do this as the items are usually overpriced junk that I do not need, but occasionally I do donate to a coat drive or some other good cause.
I hope this is helpful.