That's all part of the Airpods experience for me. Randomly have to reinsert into the case to get both earbuds working, devices I've connected to won't work if I've connected more devices, if I reboot from Linux to windows I have to drop them and re-pair them (I assume they pair based on a device id?), sometimes they don't charge but it's impossible to tell because when I open them it just shows yellow. Maybe it's because I have the first gen and no apple devices, but I really don't care for them.

My wife's soundcores work great.

My Bose over-ear are a much better experience.