Yes, ofcourse.

With LAME 3.96 VBR-0 (--preset extreme; scene standard) only 11 out of 100 people are able to differentiate with original (in this case CD quality). With LAME 3.96 320 kbit CBR (--preset insane; highest quality possible with LAME) only 6 out of 100 people are able to differentiate with original (again, CD quality). Whereas the size difference between 320 kbit CBR and VBR-0 is considerable.

Therefore, I'd encode to --preset extreme or go with FLAC. Because if you care for that insane quality you might as well keep it lossless.

Older MP3s might have different, worse quality, such as 192 CBR (previous scene standard) or older LAME versions. There are also more MP3 encoders and decoders, and I have experienced various bugs in Apple's MP3 decoder in iPhone OS 2.x and 3.x (on iPod touch), as well as in Winamp 2.x.

I'd read reviews. Pick the one I like most. Try it in store. Preferably on the target device(s). Or order via internet, if don't like, send back.

Then you're not an audiophile (anymore) and will never become one (again). I mean, in the long term it isn't worth it to damage your ears, and its then rather unreasonable to buy high quality headphones. Age also has influence on hearing capability, as well as other factors. E.g. a blind man typically hears better than an enabled person. If you go to a concert you may better wear earplugs. And the bass you gotta feel, not hear, that is where headphones are an itch of a tease. Although I guess that counts a bit less for your genre.