Is it even worth carrying and using a portable amplifier with an IPOD classic?

Everyone places their own value on their perceived improvements in sound quality.

 

I'm my experience portable amps are not worth thee trouble or expense.  I used to run full sized and portables straight out of my tiny little iPod Shuffle and thought it sounded great and had plenty of volume for my listening tastes.

 

But then I'm one of those weirdos that listens to music instead of his gear.

Well in the winter time, you can put it in your front jacket pocket and it's not that big of a deal.  I wouldn't bother carrying it around in the summer unless I was wearing cargo shorts.

There is a difference. It depends on how important that difference is to you, and how much you perceive that difference. 

 

For some guys, needing a portable iDevice DAC + Amp is essential. They know they are getting the best they can at all times. For me, that's way too much hassle, so I use earphones that are good straight out of an iPod. But I do carry portable gear with me and set up at work, coffee shop, hotel...

 

The difference your amp makes depends on your earphones too. Impedance matching, sensitivity and many other factors depend on how much mileage you get out of an amp. For me, the differences are not drastic enough to where I want to tote a brick on-the-go. But that is entirely up to you. 

Also depends on which headphones you're using. If you travel with a high impedance set of headphones then an iPod alone can't really run them. 

Completely agree with this! For me the EQ2 setting on an E6 gives a bit more bass in a way I prefer to the bass boost setting on my iPod. It's only a stop gap until I can afford a better amp but I enjoy my music much more with it than without. I've not had chance to try any bigger amps yet but if they improved the experience substantially I think I could tolerate a bit more hassle.

But traveling is another story. HP cases are too big to carry in my carry-on or backpack, if I have to add the extra bulk, I definitely would say no.