I need Sound Card and/or Headset Recommendations

Onboard audio is more than fine.

I'm looking to start using 5.1 surround sound in the near future.

HTOMEGA for sound cards

I'm looking for specifics, like the X-fi Titanium HD or a Z series card. Onboard sound is not something that I am looking to keep simply because it is lacking on my current motherboard(sounds bad)

Depends of what are you looking for:

A- Sound for gaming

B- Sound for Music and movies.

Also: Do you mind your headphones leaking sound to the outside or you want them to be hermetic?

I am using an Asus Xonar Essence STX for soundcard and for heaphones a pair of Beyerdynamic DT 880 Pro, which is better for music and movies but not gaming oriented really.

bump

I recommend these...
Encore ENMA
ASUS DSX / DS

you wont actually need to spend a lot on soundcards, your ears may not be that trained to hear minute differences it gives. those I've listed is enough for the average movie goer and gamer. I personally use ASUS DSX.

the more pricey soundcards will only give minute difference, it's not worth it.
if you can hear the difference between the bitrate of music file types, then you should be buying a full external setup not an expensive soundcard.

People still use soundcards? The last time I used those was early pentium machines. Since then some kind of onboard surround sound chip has been on every pc motherboard.