
Apple
AirPod Pro Series
Apple-integrated, great ANC, but fit issues & poor Windows support.

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I like LinkBuds S but the XM5 do sound better. The only battery issue I have is they don't last as long as the XM5.
For the price, yes.
I also have tiny ear canals, so tiny that any kind of silicon tipped earbud just simply won't fit or feels very uncomfortable. Were the JBL buds and airpods woth silicone tips or semi-open? I recently took a look at a lot of semi-open buds to make a purchase. Otherwise I would suggest semi-open buds, and particularly the standard airpods (since anc don't matter you could just go for the standard airpods 4, not the ANC ones). The aipods have a good mic. There are several JBL buds that are semi open. The JBL tune flexes come as the standard semi-open version in the box, but also interchangable silicone-tips. The mic on these are decent for the low price of 40-50$ depending on your region. The sound quality overall is passable and they have ANC, but it's basically non-existent. The samsung galaxy buds 3 also allegedly have a very good mic. The non pro version are without tips that enter your ear canals. These have also recently gone on sale for about 90$. Many do, however, claim that there is a problem with the fit. They seem to be larger than the average earbud, and this causes them to slip out for people who have smaller ears (small ears! Not ear canals!). For others the larger size seem to work better and they sit snuggly, but these seem to be for individuals with larger ears. There are other brands as well that have semi-open earbuds. Nothing ear stick is also quite good and have a decent mic. But I would warn that these are a nightmare to clean due to the mesh used on them. Eventually these get a problem with sound volume or break from trying to clean them (I had to get new ones because of this) There are of course earbuds with silicone tips that have XS sizes, but I have not looked at these since I never found any of them to work for me. A mandatory note is that there is also a very popular category of open earbuds that can also be very good, but I have never tried any of them.
I just got buds 3 (none pro) free with my phone purchase, they are okay but compared to my bose quietcomfort II (2022 model) sound like crap. They are still comfortable and the Bluetooth connection is better than Bose to connect quickly.
I have the Buds3 FE. The most annoying thing is the material they are made of. It's this sort of matte plastic that has 0 grip on your fingers. Especially in winter, if you have dry hands. The triangular shape does not help. I use earbuds only when I really need them, and never for extensive periods of time, so they are absolutely ok for me. But they would drive me crazy if I had to use them more frequently
Samsung's Buds3 FE fits in your price range, and have great ANC, fit and sound. The ANC on them is better than the buds3 pro! (but not as good as buds4). The eartips and shape Samsung uses is supremely comfortable, but YMMV. Otherwise, you could save a bit more cash and try the OnePlus buds 4, which are great all-rounders.
For me, wingtips or hooks are pretty essential in the gym for the best fit otherwise they'll just fall out. Foam tips can also really make a difference but they'll quickly ruin in the gym The Soundcore X20 work really well as do any of the Bose buds with wings. I also have had good experiences using the OnePlus 4 with Foam tips or the Galaxy Buds 3 with azla crystal tips. The majority of other buds just fall out or need readjusting often.
I personally like the Galaxy Buds best here with Nothing a close second. I haven't actually tried the freebuds 4 enough to comment however

Apple
AirPod Pro Series
Apple-integrated, great ANC, but fit issues & poor Windows support.

OnePlus
Buds 4
Budget ANC king, but no wireless charging & windy transparency fails.

Beats (Apple)
Fit Pro
Workout secure, Apple-friendly, but wing-tips tear and case feels cheap.

Anker Soundcore
Sport X20
Value workout buds, secure fit, but connectivity can be iffy.

EarFun
Air Pro 4
Budget champ with great sound/ANC, but transparency has static.

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Technics - EAH-AZ100

Ranked #1
Beats (Apple) - Fit Pro

Ranked #1
ISOtunes - PRO Aware 2.0

Ranked #1
Apple - AirPod Pro Series

Ranked #1
Shokz - OpenFit Series