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I think it's always a good idea to keep your resume updated because you never know what can come your way.
Three years ago I was in a bad job, it was boring, and it paid poorly, the company had issues, and the benefits weren't really worth it either. It was hard to leave though because I really liked the people I worked with. The job I moved to was a really sudden opening, so it helped that I had an updated resume. I interviewed and started two weeks later. It seemed like a good one until I actually moved. The pay was about $15K higher, the benefits were immediate and awesome, and while the career path was different, it seemed like fun.
"Seemed" being the operative word.
Two and a half months after I started there, the company had some issues and had to undergo a huge reorg. A lot of people got moved to a sister company and a lot of people there could see the end and left the company all-together.
I was really fortunate that someone from an entirely different company that I had met at my first job remembered me and specifically called me then to tell me about an opportunity opening up. I happened to have an updated resume, went in for the interview just to check it out, and ended up leaving Company #2. The pay increase wasn't as drastic as the other one was, but the benefits were still good, and it was a good, solid company.
I think that last move was the best thing that has happened to me and I'm really happy things worked out the way they did because I've been with Company #3 for the last 2 years and wouldn't have it any other way.
It definitely pays off to keep your resume updated. Even if you don't want to leave your company, if you are a good employee that your current company wants to keep, you can use your other offers as negotiating chips to get higher pay if you stay. I've seen it happen a few times.
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