We used Eartec, single ear headsets and were very happy with them and the performance! Good advice about removing the batteries when not in use, and having a spare set of batteries as well. Pretty simple actually.
There are work arounds or prevention measures that can all but eliminate the sets accidentally falling off and/or overboard. We fashioned a "home made" lanyard setup to ensure that the headset could not fall overboard. A person could also use an elastic "sports" style headband or a hat to help them stay in place if they found that to be a problem. We didn't need that solution as for us they stayed in place even during anchoring. We liked the single ear model as we were able to hear "others" (like dock hands) while still hearing (and being to speak to) our partner. They gave us the ability to instantly communicate, giving an accurate clear message, in a calm and reliable manner. At times this could be invaluable (IMHO). Hand signals and/or line of sight voice communication can be difficult to impossible on some boats.
We used the Eartecs for 2 full seasons before selling them to another TF member (having recently sold our boat with our old (still working) sets (different brand)), and they were basically in like new condition. We stored them in their case when not in actual use. Each season was over 3 months of continuous boat use and we used the headsets for docking and departures, anchoring, and taking a mooring, so they had lots of use.
Just a customer, no affiliation as an FYI.