Quick update.
I went to a local shop that sold the Westone star tips.
Holy hell comfort!!
I had the opportunity to test out all different sizes that were available and ended up choosing the medium sized long flange style tip that are color coded "red"
The diameter seems to fall right in between the medium and small gray olives of Shure's.
Some differences in sound I have noticed.
First the bad: isolation does seem to suffer just a tiny tiny bit compared to the triple flange tips. Also the bass does not impact as hard just by a tiny tiny TINY bit.
Good: but both are more than acceptable for the amount of comfort offered by these tips. I no longer have to constantly fidget with the placement to find some comfort which was hugely distracting and was a huge distraction to the overall experience. Now I barely feel them my ears!
Another huge plus of these tips is the treble extension that these tips somehow makes possible. In lack of a better explanation, say for example the trebble extension of the stock tips extended up to back off your eyes. Now you feel as if the treble extends all the way to to temples of your head without ever being too harsh or sibilant. I guess that's what the airiness of the tips feel like.
Also, because of the long tip design, even if you dont have that perfect seal that sometimes causes a pain in your drums when you yank them out (as if the pressure was going to turn your eardrums inside out), the isolation is just as good. The perfect airtight seal is still there, it's just that when you pull them out of your ears there is much much less pain when doing so. When I was using the stock tips, in order to find that seal I had to use a slightly larger tip which was super uncomfortable and felt like it was stretching open my ear canal, which would result in a headache after an hour or two.
As for the recommendation for custom fitted tips, I'm definitely sure that they do offer the best isolation, the best bass response, and the best comfort, but unfortunately I'm in hong kong for now and shipping costs will pretty much triple if i were willing to receive anything in a reasonable amount of time. After i move back to the states i do plan on getting custom sleeves. But until then, i think i have found quite a satisfying fit
Thanks everyone for reading this far
Back to catching up with this thread. Currently on page 62 lol