I switched from Bose to Shure. As said, no batteries, small, better protection from ambient sound.
For me the real plus is that even the less than top of the line Shures have much, much better sound reproduction. If you listen to music that requires good reproduction, no comparison for quality.
I use the E5's. Thinking about upgrading to the newer E530's. I don't happen to like the PTH. Too much wire. Just me. I find it quite easy to take the triple flange ear tips in and out.
As to comfort? A very personal thing. For me, the triple flanges are fine on 15 hours runs trans-con -> trans ocean.