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I've currently using the W50s and has long appreciated the warm, lush tonality of the westone IEMs. As an upgrade, I am considering the W80s and ES60s that are around the price range.
Between the additional drivers of the W80s and the custom fit of the ES60s, would the improvements in the sound of the W80s be considered incremental to the W50s when compared to improvements in fit and sound isolation when moving to a CIEM?
Good question. Not sure if you have read my W60/W80/ES60/ES80 reviews, I did lots of comparison, especially in the latest W80 and ES80 reviews (you can search on my blog here). As you probably aware, W50 was (in the past tense since it has been discontinued) their basshead level IEM. With an EQ I was able to bring the bass down to make it sound closer to W60. To my ears, W80 is an upgrade to W60, while ES60 is a side-grade geared more toward audiophiles who want a more balanced and revealing signature. ES60 is not CIEM version of W60, and ES80 is not a CIEM version of W80, both customs are tuned differently.
With all that said and considering you are still getting a custom-like fit of W80 (probably still one of the smallest and the most compact 8-driver universals you can find), based on your previous experience with W50 model you should look into W80 as an upgrade, and not ES60 or ES80. Another advantage of W80, if you are not happy with it, you can return or sell it. With custom, I'm not sure if there is an owner transfer policy or reshell fee for a new owner when you sell it.