[Gummy]

It's been said that $1 headphone = $8-10 in speakers for the same quality.

What about headphones and in ear monitors?

Something like $1 headphone = $5 IEM?

I have the e2 and they don't sound as good as Grado SR60 for the higher price.
How high do I need to go to get the same kind of clarity? (and then do the math from there)

 

[Kirosia]

Canalphones are a compromise, a full-size phone with the same performance will usually be less costly. I had the er-6 and they weren't as good as the MS1 in the vocal department. (But were great for portable use) I would consider them comparable though. I think you should go straight to the er-4, considered the best bang for the buck canalphone. (You can get them for like $200 new/used)

 

[kyrie]

Canalphones don't really compromise that much in terms of cost. I'd say about
$10 full size = $15 canal. The exception are the Ety ER4*, which can compete head-to-head with equally or greater priced full-size headphones. Keep in mind that to some extent, the ratio might be swayed by your musical preference as well. If you put lots of value on full, realistic low bass, then it is likely that you won't be satisfied with canalphones until you go Shure E5 or higher.