Jen
I assume it is different for male and female wearers. There is some evidence that it is healthy for people with male genitalia to ejaculate regularly (which does not make it strictly necessary per se, but a good chastity routine should be healthy, so it kinda sets a lower limit on permissible ejaculations). Note that those ejaculations do not necessarily have to come through masturbation or sexual intercourse, many young males have spontaneous emissions in their sleep, particularly at the onset of puberty or after long-term orgasm denial, and ejaculation can also be induced through prostate stimulation. In case of the latter, it is possible to also induce orgasm, but from what I have heard (no personal experience putting anything but suppositories up my butt), it is a lot easier to separate from pleasurable orgasmic relief than ejaculations from penis stimulation. Male chastity enthusiasts usually use the term "milking" to refer to that procedure. And even if orgasm were necessary for those healthy ejaculations, most guys tend to want one a lot more often than they need them.
For me personally, I still have not set any rules in stone, I am still seeing what works for me. Currently, my plan is to only be unchaste one day a week at most, on a weekend if possible, preferably on sundays. That does not mean relieving myself every sunday though, I prefer to plan things through the week ahead and for this sunday my mind is set on "rather not". Since I want to avoid health risks and/or the chance of dirtying up my bed though, I do want to have a deliberate emission at least once a month.
Fortunately, despite having masturbated out of habit for years, it has not reached a level of addiction where I do not have the clarity of mind to make decisions with my head on whether I want to orgasm or not. The device is mostly an upgrade over pure willpower to handle momentary lapses in judgment, and having to reach for the key (or something to open the lock with at least) buys me time for my will to take over again. For the same reason, I trust myself to take off the device even when I am not planning to have a release right now, as long as I am not exposed to any stimuli that would cloud my mind.
