Oh man; this thread is the holy grail of TWS. I've tried so many! Here are my quick thoughts on all of the pairs I've used over the years. Note: I have small ears, so fit is a challenge for me:
AirPods v1: Easiest Bluetooth headphones to pair ever, especially on a Mac, but surprisingly easy on other devices as well. Sound is okay, not great. Isolation is absent. AAC only. Control system kind of stinks; taps are worse than buttons. Phone calls are God-tier; could use these anywhere. Battery life okay at 5 hours, though in the past it was the best you could get. Being able to use each pod independently made this feel longer. No transparency mode or ANC. Case was pocketable; fit in the coin pocket. Recommend.
Bragi Dash Pros: A bit challenging to pair. Even more challenging to update. Sound is okay for $100; poor for $300. Bass is basically absent, mids and highs a bit muddy. No separation and shoebox-sized soundstage; worse than other IEMs. I'd say the sound profile was below-flat. Isolation was very good. Control system was very good; 4D menu was well beyond its years. AAC only. Abysmal for phone calls; troublesome indoors and unusable outdoors. Also, phone calls were imbalanced, which was annoying. Battery life okay at 3.5 hours; using its features brought that down a bit. Transparency mode was God-tier; nothing comes close to it. Case was a brick; not pocketable. They were waterproof, but they also had terrible QC; showering with them broke them twice. Didn't use the fitness features; already had a smartwatch. Sadly, do not recommend.
Custom Bragi/Starkey Dash Pro. A massive rollercoaster ride. Same as Dash Pro, but with more bass b/c custom. Sound was actually okay after using the Mimi equalizer that came with the app. Heavily depends on how well they fit, which is an ordeal. I needed to use Otoferm to wear these every time, but my ears typically run dry. (I have to use lubricant for my custom-molded sleep ear plugs, too.) Massive pain to get repaired; expect two weeks wait time every time. Isolation is unmatched, though. You can tune everything out at one tick above minimum volume. Insane. That's why it was such a rollercoaster ride. They were so, so good to use on flights, issues aside. Considered ordering another set to deal with the battery issues, but that plan died when Bragi did. Sadly, do not recommend.
Jabra Elite 65t: Easy to pair; not as easy as AirPods. Easy to update, but took a while. Sound is good, but not great. Like AirPods, but better. AAC only. Control system was fine, though physical buttons can be tiring on your ears. Fit was a massive sore spot for me; could not wear them past two hours. Comply tips sort-of worked, but they wouldn't fit in the case if you used them. Call quality was great, but struggled outdoors. Battery life okay at 3.5 hours, though this is low-end now. Transparency mode was passable; things sounded slightly robotic. Case was pocketable; fit in the coin pocket. Recommend...if they fit you.
B&O Beoplay E8: Easy to pair. Easy to update, but took a while. I didn't like the sound profile. Heavy-ish bass for no reason. Felt artificial. Mids and highs okay. Small soundstage, as expected. AAC only. Control system was annoying; don't remember much about it except it annoying me. Fit was amazing, especially with normal-sized Comply tips (which they used no problem). Call quality was absolute trash. Transparency mode was trash too; everything sounded underwater. Really liked the case, but it was big. Not pocketable. Do not recommend.
Sennheiser Momentum TW: Easy-ish to pair. Easy to update, but took a while. LOVED how these sounded. Bass was big, but not overbearing. Mids and highs were crisp. Great clarity, and great separation. I'd say the sound was light V-shaped. AAC and AptX supported. Fit was amazing, especially with Comply tips (which they used no problem). Call quality was not great, but passable. Fine for using indoors. Transparency mode was fine. Life-like, but quiet. Really liked the case; felt quality. Pocketable. Battery life was fine at 5-ish hours, but they have a massive bug wherein the earbuds essentially never enter sleep mode. Consequently, they need constant charging and will not only discharge rapidly when the battery in the case is dead, but they will also pair with your phone while they are in the case. The number of times I tried to use the headphones but couldn't becasue they were either dead or close to dying was too damn high. Updates have addressed the issue (they sort-of sleep now), but it's still an open issue. No idea how these got the ok for Production with this regression open, but it is what it is. Recommend.
Samsung Galaxy Buds: Very easy to pair, especially if you have a Samsung phone. Easy to update. A lot of people seem to like how these sound, but I don't think they sound that great. Mids and highs sound artificial to me. Bass was lacking. Tried hard to find it with a bunch of different tips. AAC and Samsung Scalable Codec (SBC-derivative) only. Fit was really good; not as so-comfy-you'll-forget-them as the Senns were. Call quality was not great, but passable. Fine for using indoors. Transparency mode was passable; not great. This feature, along with a bunch of others, only works if you have an Android device. Everyone sounded robotic, but I got used to them. Very small case. Very pocketable; fit in my coin pocket. Recommend.
PowerBeats Pro: AirPods-easy to pair. Updates automatically. Great sound. Nice bass, heavy. Mids and highs clean enough. Small soundstage. AAC only. Fit was great. Ear hooks could be more adjustable though. Isolation wasn't great, even with Complys. Call quality was AirPods-tier, so really good. No transparency mode. Big case, not pocketable. Stereo pair breaks up in congested Bluetooth airspace. You need to invoke Siri or Google Assistant to fix. Very annoying, but I'm assuming this isn't a problem with iPhones. Recommend.
Master and Dynamics MW07+: Pairing experience is alright. You have to take out the right bud to pair it with another device. A bit annoying, especially with Complys on. Updating experience uncertain, since they don't come with an app. These sound really good. The bass doesn't attack as hard as the Momentums do, but it is REALLY clean. Listening to jazz on these is nice, but the Senns are better for trap with that heavy bass. You hear it more than you feel it...but sometimes you feel it. Mids and highs are CRISPY. Super duper clean. Beautiful separation; better than the Senns, as the treble isn't as sibilant. Soundstage feels bigger than it really is. These support SBC HD and AptX. They theoretically support AAC, but I can't use them as such with my Mac. They still sound quite good through SBC alone, but this might deter iPhone users. Call quality surprised me. These are AMAZING for calls. Extremely usable indoors and out. Fit is really good; I can wear these for hours no problem. Transparency mode is okay, but not great. Senns were better here. Almost life-like, but quiet. LOVE this case. It's cold and unapologetic stainless steel. Yes, it's a fingerprint magnet, but it also looks SUPER cool. Very pocketable. Fits in coin pocket. Highly recommend.
AirPods Pro: Pending.