this post was submitted on 02 Mar 2026
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My primary income is W2, but I have a 1099 side gig (teaching scuba and underwater photography at a university) that usually results in me itemizing mostly because my gear is stupid expensive and I rarely make an actual profit. The write-offs are enough to let me justify spending the money on the gear to help me break even while teaching.
I do multi-year write-offs on the big-ticket items, because one underwater camera rig (camera, housing, strobes, wet-lenses, etc) costs what I make teaching underwater photography across 4-6 semesters.
I think the last time I itemized was when I was doing some 1099 work, plus changed jobs, changed employment state, sold a house in one state and bought one in another.
It was a complicated tax year.