There are really two questions to address here...
One is more about disturbing the seal when you open the watch, and yes this can result in a seal that inadvertently gets pinched or otherwise damaged, so it's good practice for any competent watchmaker to pressure test the watch after opening. It's something I do every time I open a watch.
The second is more about regular testing, and how a watch leaks. Omega recommends pressure testing once per year, and if you are regularly getting the watch wet, that would be my advice also. The seals in these watches will fail eventually, and when they do it won't really matter what depth you go to - on a serious dive or just a dip in the pool will have the same result.
Cheers, Al
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