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na blur said:

Either one will be an upgrade for sure whether your gear drives them well enough to really hear a HUGE difference is dependant on of course...your gear.  The D2000's are one of those headphones that have been on Headroom's Top 10 list for years.  I think you will like the DT770 ( 32 Ohm ) the 80 Ohm version will work fine with your gear, but why chance it.  Get the 32 Ohm version and you will be set unless you have a convincing argument why the 80 Ohm version is better.
 
If you are going to be able to save up for a few months and you really want to go open vs closed the DT990 ( 32 Ohm ) will be a very nice upgrade.  Patience always pays off when it comes to just about anything and audio gear is no exception.
 
Both the DT990, DT770, and D2000 are incredibly comfortable headphones and when you try them on and give them a listen you will probably say "why have I not done this earlier?"  I have no doubts on the comfort improvement.  Just be sure to make a good long term decision.  The DT990 and D2000 are going to be your best improvement headphones in the long run, but we can only take the horse to water.  You are going to be the one drinking from the water.
 
So put your hands in your pockets for a few months and decide what type of sound you like:
1.)  Do you want an incredibly smooth, warm, and closed headphone?  It will also have nice bass and very clear mids to highs.  If so, then go with the D2000.
2.)  Do you want an incredibly clear sounding from bass to highs headphone?  It will also respond really well to amping eliminating the need to upgrade for months possibly years.  It is also an open can giving you that super tight bass response.  If so, go with the DT990 ( 32 Ohm )
 
You really cannot go wrong between those two.  I bet you will like either.

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YOU are costing me a lot of money with all your helpful advice, =)
 
The DT990 (32ohm) seem like the best value/sound for what i'm looking for, but I have a feeling if I get them i'll rarely listen to my Grado 225's anymore.
I'm thinking that the closed DT770's will provide me with a much different sound/feel than the Grado's, and allow me to listen to both.
With the closed D2000 at $150 more than the DT770's, I think that is too steep, and it doesn't seem like they are twice as good as the DT700's (are they twice as good?).
 
In any case, the DT770's are in the lead. They have two main versions:
1)DT770 Pro 80 Ohm
2)DT770 Edition/Premium 32 OHM
 
From the Beyerdynamic site:
[[[Difference between DT 880 PRO - DT 880 Edition - (PRO vs. Consumer)
[[[The DT 770 PRO is designed for use in studio and on stage for professional use. It's headband has a more rugged construction (thicker material) and gives a more secure fit for the listener in [[[comparison to the DT 770 Edition. This provides a better fit and causes also a more powerful compressed sound which is necessary for professional applications in studio, OB and FOH. The [[[DT 770 Edition therefore is designed for easy listening. The headband provides a long wearing comfort for hours, causing the DT 770 Edition to have a more transparent and open sound in [[[comparison to the DT 770 PRO.
[[[The differences of both headphones are not huge in mechanical design, but only that small change causes a big difference in sound and application.
 
Seems like the Edition/Premium version is a bit better, but also $50 more expensive. Ive also read that the 80 ohm version has better base, which I like.
My local retailer has the Pro 80ohm version in stock so I can try it on and possibly return it, but can order the 32 Ohm version (no try on/return).
I'm going to get the Fiio e10 DAC/AMP when it comes out, so maybe the Pro 80 ohm version will be fine.
Is THAT convincing enough why I should get the 80 Ohm version??
 
Just running this by you in case you have any further insights (or in case you want to convince me to spend more money on something else/better). Thanks for the expertise and help!!