In the run-up to Y2K, I was all over the US, upgrading/replacing data integration engines for larger healthcare and utility companies. After around a year of being on the road for weeks on end, supporting one site locally and 3-5 others remotely from my hotel room in the evenings, I finally got smart and caught on with a big hospital system to run their integration team.
Gave my current employer 4 weeks notice, as this would allow me to get my main client site in Arkansas through their go-live. Thought this would be a great way to end up for them. On Thursday of the final week, go-live week, I received a call from a colleague who was also in his final week with the company, saying "Check your credit cards ... mine have been cut off".
I checked, and so had mine. Amex, phone card, everything. 3 weeks of hotel, long distance bill, car rental, etc ... and I was on the hook for all of it. I went to my contact at the client site, explained the situation. He was livid. Insisted on paying all of my bills, and charging it back to the my soon to be ex-employer, with a significant markup for being idiots. Go-live was flawless, and I hopped the plane home on Friday, footloose and fancy-free.
Haven't considered a traveling job since.