I had a $12,000 theft of a trailer stolen with police reports and insurance claims. Insurance only covered $3000 due to a special limit on trailers in the states of OK and TX. I have to replace the trailer at a cost of $9000. I will show a loss of $9000 on my taxes. Do I add the cost of the new trailer to that amount to show an $18,000 loss? Should I replace the trailer now or hold off until next tax year? If I'm self-employed with a tax ID, how do I file this to not raise flags? Should I let the business buy the replacement trailer to claim it as a depreciable asset?

September 29th, 2023

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