I used to have stress tests as part of my ant file, so I could run those tests every night, if I wanted, and I would run them when I was making any changes, or testing a possible new change, that would in one way or another impact what I was testing, to see if there was any improvement.
I think how often would depend on your environment.
If you can't really stress test in development then you may have to wait until you get to QA, where you are testing just before you go to production.
I think the sooner you do it the better, as you can find problems and fix them faster, since you know it worked two nights ago, last night it failed the test, so there was some change during the day that caused it.
I used junitperf for many of my stress tests.