Blon BL-03: My first IEMs, and my daily beaters for 3 years. Wore them everywhere while doing anything. Fun, bassy sound that I still enjoy to this day.
Etymotic ER2SE: My second pair, primarily used them for critical listening and for their isolation. Still the most “detailed” set I own imo.
Jabra Elite 7 Pro: Picked these up a little over a year ago. Primarily used for their convenience and ANC for exercise, though they sound pretty nice too and are probably my best or second best fitting set.
7Hz Zero: Bought these last year while they were getting hype as a budget killer. Nice, balanced sound, though they don’t see much use nowadays, as they don’t really beat any of my other sets in their respective niches.
AirPods Pro 2: Picked these up earlier this year after transitioning over to the Apple ecosystem. Great features, and probably the best or second best sound quality out of the sets I own. I use these the most nowadays because of how convenient and feature rich they are on top of their nice sound.
I've worn them for those kinds of durations with little discomfort, but they're really annoying if you have to take them out then put them back in with any kind of frequency. Microphonics are also an issue if you're gonna be moving around a lot. Could try wearing them with the cable wrapped over your ears like other IEMs, which helps with microphonics, but it looks kind of awkward.