I'm not sure if you read these emails directly, but thought I'd give it a try.
I just thought I should share my experiences with you as a many year customer of Road ID, and as someone who's needed to have their Road ID used by first responders when I crashed in a bike race. It seems like a good time to, given you're trying to re-focus your efforts after feeling a little off course.
First off, on the customer service side, I've had really good experiences both purchasing my Road IDs, and when mine was used. The EMTs got what they needed, my wife was contacted quickly, and your email follow ups were appreciated (months later anyway, when I was coherent enough to read them), as well as replacing my ID for free that had been damaged in the crash. It was a really "good" experience as much as I can say a broken neck/brain injury can be. :)
That was back in spring of 2015, so I'm not sure how things have changed since then, but I hope you can maintain how things were at that point, as you really nailed it.
My other thought was on the Sidekick IDs, as I can understand the headache of supporting so many devices with so many different wrist bands not being something scale-able, you also mentioned frustrated users replacing devices and then not being able to switch their Road ID to the new device, and since people are often so much more vocal with negative experiences I wanted to give you the other side of that.
I upgraded from my Garmin 920xt to the Garmin 935xt and was very excited when I saw the Road ID Sidekick pre-order for that watch get announced. with the optical heart rate built into the watch, and the Sidekick, I was consolidating down from my watch, a Mio optical wrist heart rate bracelet, and my Road ID bracelet, down to just one. It's been great, and since I wear the watch 24/7, my ID is also on me at all times.
I wish a company like Garmin could standardize on the widths of their watch bands to make it easier to support, but they're only just starting to manage that with their watch chargers, so I'm not sure how likely that is. That said, since you're continuing to support the Apple Watch, what about supporting whatever the current high end triathlon Garmin watch is? They're only updated every couple of years, and from looking around at my triathlon friends, users don't upgrade them very often, so it seems like one where there wouldn't be so many turnover pains as in the Fitbit or Vivoactive products.
Anyway, I hope this finds it's way somewhere useful, and thanks for your help when it was needed.
Attached is a photo of my well-loved Sidekick 935.