[slv77]

Business expenses must be ordinary and necessary to be deductible. A roofer would have a hard time justifying deducting a boat under the rule but a commercial fisherman wouldn’t have trouble.

Entertainment expenses are no longer deductible with recent tax law changes with few exceptions. It would be difficult today to get a CPA to sign-off off on a lot of what may have passed previously. A decent write-up can be found here - https://www.thetaxadviser.com/issues/2023/nov/navigating-aro...

[EGreg]

* However, a taxpayer’s trade or business must be considered. For example, a theatrical performance, which would normally be considered an entertainment expense, would not be an entertainment expense for a professional theater critic attending the performance in a professional capacity (Regs. Secs. 1.274-11(b)(1)(iii), 1.274-12(a)(1), and 1.274-12(b)(3)).*

This seems to support what I’m suggesting