Chastity and orgasm denial discussion

hi everyone, I’ve been into chastity since my early teens, and now at 23 I’m considering getting a device. I’ve spoken with others and found someone willing to be my keyholder, though it will be a long-distance arrangement. This is where I have some questions. My first worry is that I am uncircumcised, so I need to think about hygiene and which device works best for 24/7 wear. Once the break-in period ends, I won’t have my key and can’t remove the device to clean properly. Secondly, not as big a concern but still on my mind: what are some ideas for things a long-distance keyholder can do online to tease or punish?