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Please excuse my rambling. I'm just a young man who, as a lover of music, has as desire to learn more about audio through experience. With just about any other decision, one could weigh the cost benefit by garnering objective facts, but not with audio and certainly not on Head-Fi. Part of me wants to dive into the FOR SALE forums to buy and trade until I have come to some kind of conclusion to these questions and another part of me says to never buy audio gear ever again.
Can anyone offer some guidance? What are your setups and why did you choose to or choose not to upgrade your 598 setup?
Walden, I feel your pain, but let me offer some advice, as a relative newcomer to Head-Fi. There is a TON of noise on Head-Fi, but if you carefully read the reviews of products from the more experienced reviewers, you will cut through to the content. As a great example, look at the recent review by ClieOS on the iFi products:
http://www.head-fi.org/products/ifi-ican-headphone-amplifier/reviews/9065
This reviewer is a stand-out, in my opinion, and reading stuff from Head-Fi'ers like ClieOS is good way to learn about various products w/o having to buy them all. BTW, this fellow makes interesting comments about the O2 - he's a fan, for sure, but that doesn't mean you have to trust that person's judgement.
At the end of the day, you will need to make a 'buy' decision and try some stuff out - you won't really learn more about this hobby without exposing your ears/brain to new gear. I don't have either the O2 or anything from Schiit, but from the reading I've done here I can't see that either setup will be a bad choice.
If spending $200.00 on a DAC/amp combo is too great a risk, then stick with your Dell desktop and spend some of your newly acquired cash on music and enjoy your HD-598s - I love mine - sometimes
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BTW, in answer to your second question, why did I upgrade? Well, I already had most of my Head-Fi setup (see my signature) and I wanted to try some phones with a different sound signature and experience something new.