I clean the earwax off/out of them when I see it or the sound is affected (I wear deep insertion IEMs with tri-flange silicone tips), but otherwise just replace the tips when they wear out a couple times a year.

I’d probably just say something non-pressuring but supportive like “I know with everything that is going on recently that things may be challenging for you right now. If you need anything please don’t hesitate to reach out to me and I’ll support you in any way I can.”