I bought a pair of L500 mkii's since first replying to this post (So I'm updating this post)
The L500 MKii seem to be pretty much the same audibly as the L300's. I have an extra pair of regular L500 pads (Same pads as the MK2 L500 pads) so I can listen to the L300+L500 pads and L500 mkii and compare: they both sound the same and I can use the same EQ for both.
Pretty much if you switch out the headband on the L300 + L500 pads ... you have a L500 MKii minus the replaceable cables ... though I've yet to have problems with any non-replacable stax cables in the past either. So I'd say if you want to save money: just buy L300. (But get a Topping EHA5 or Stax 353x or 400S if possible instead of the 252S) The cable is a bit more bendable on the L500mk2 but audibly I don't really hear any difference.
As far as L300 with replaced aluminum headband and L300 pads vs stock L500mkii ... Without EQ the L300 sounds more accurate than the L500mkii out of the box. So if you don't have access to EQ: L300 is probably better. Comfort isn't bad on the L300 - yes your ears might possibly touch the inside depending on your ears but I never had any problems with it. I'd say you'd be less prone to sweaty ears with the L300 pads though ... I feel like the L500 pads are more comfortable overall but sometimes I like the L300 pads better personally (maybe I'm just used to them?)
With EQ ... it's a tossup: I think I prefer the L500 pads but I've tried comparing other days and sometimes prefer the L300 for sound. It's close so I doubt it really matters even if mixing. They sound MUCH better than AKG K371 and Truthear Zeros which measure pretty 'flat' when they all are EQ'd. Bass with EQ sounds much better on the Stax than the K371 or Truthear Zeros to me too. (I have to have the volume on Stax down about 8-12 depending on my EQ setting though for such bass - but it doesn't distort, but I do need the EHA5 to be on the higher power setting with that much EQ)
I would like to try some higher end Stax but I guess I've just never had a chance and considering I like these headphones more or the same as my previous Raal SR1A's and Jade II's and better than CRBN/Utopia ... I'm pretty happy with the L300's/L500mkii. I just don't know if after EQ the difference would be that much better or at all on a 007 or 009. Maybe one day I'll have a chance to check them out but I'll probably wait to see if any Jade III's or something new under $1500 pops up in the next few years to try out before that.
*Update: I got Jade II's again - Prefer Jade II's over L300 or L500mkii. Not a huge difference: all are good but comfort-wise I prefer the jades and the overall sound after EQ. (Though sold them all and went to 7hz Zero 2's as they have more bass and sound flatter overall. The Electrostatics are nice but to me not worth keeping. Picked up a pair of Ananda Nano's and really like them though. Definitely reminds me of the electrostatics but with bass.
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