I'll make my best ;)
Well, it is not recommended to plug high impedance headphones directly to a normal Laptop, and it is not recommended to pair a high end ultra detailed headphone with a cheap on-board DAC/AMP combo. This will result in a noticeable loss of sound quality. In this case is better to choose cheaper headphones and getting a separate DAC and Amp.
To answer your question about WMA Lossless I think this is something important you need to know:
Then you don't need to care much about how your music is digitally stored in your laptop, just be sure of having good transcodes. I think good Mp3 (320Kbps) is a great place to start; improvements over this format are not easy to perceive and if that is possible, then you won't find a huge sound quality improvement.
That said, the recording quality (which depends on how music is produced) is a really important link in the sound quality chain (as important as the headphones itself)
You can read about "The Loudness War" and here you have a great Dynamic Range Database where you can sort albums by artist:
I've found all this information really useful in my way of getting that WOW factor that you are looking for.
Sometimes it is quite hard to accept that the music you used to listen is not properly produced, and you can't get enough transparency, separation or high quality timbres out of that recordings, no matter how good your setup is.
Another important thing to decide is what sound signature fits you better, bright headphones pair well with high quality recordings but not with most modern, over bright (and/or) highly compressed recordings. That is probably the main reason why there are so many people complaining about sibilance on DT880, DT990, K701, HD800, T1, etc.
It is a common error to think that more expensive and technically superior headphones will simply sound better. Pairing a detail monster with wrong recordings make you feel you have spent a lot of money for an awful sounding experience. It is really important to choose the correct sound signature for your recordings and tastes.
Another thing you should try once you have headphones with big soundstage is high quality binaural recordings.
Edited by Me x3 - 11/17/13 at 9:33am