My wife and I both have professional jobs and make pretty good money. My wife also got a part time job (W-2) at a ski resort this winter, mostly for fun, and was paid hardly anything (and only worked 10 days). She paid out of pocket to stay in the cheapest hotel on site on the nights connecting her work shifts. As a sidenote, for whatever it's worth, the hotel cost more than she earned on the resort, so with respect to that job she made negative money (but both the hotel costs and the income at the resort are drops in the bucket compared to our primary incomes). Also as a sidenote, the ski resort is in the middle of nowhere, and if she didn't stay on that resort she'd have had at least an hour drive each way, in potentially dangerous conditions, from the next closest options. The resort gave her zero accommodation options as part of her compensation, she was on her own to pay out of pocket, which is why she did. I should also note that I sometimes tagged along and shared the room with her, if that is relevant (but it was the smallest cheapest room on site).

* Is the hotel cost deductible?
* If yes to the above question... what year should the deductions apply to, considering that the hotel stays took place in 2019, but were all paid for in 2018.