Hey Now,
I am using the following from my iMac:
iMac >> Pure Music/iTunes (Apple Lossless/HD Tracks) >> M2Tech HiFace or RWA Transit (USB to SPDIF converters) >> Twisted Pear Opus Balanced DAC >> Audio-GD Roc balanced Amp >> Audio Engine A2 or balanced headphones Grado SR325/Fostex T40v1 or SE HD650 with a couple of nice cables and power supplies. It's all good 8^).
1. Lots of choices. I have owned/own Aune modded ($120), Zhaolu modded ($95), Maverick modded ($150), Vivid Technologies V1 ($75) Valab DAC($130) and settled on the Twisted Pear Opus DAC ($350). All used, purchased off the FS forums. Very happy with the Opus. You can spend lots more for better gear. I had an opportunity to audition Audio-GD Ref 7 through custom/top tier amps and top tier headphones like HD800, PS1000, LCD2, HD650, DT880/600, Headphile, AKG K701, AH-D5000, GS-1000 (that was one fun CVG meet). I would love to have that equipment but can't afford/justify it right now 8^).
2. I settled on a pair of used AE A2s ($130), good price and sound terrific. There are lots of choices now.
3. The Aune, Zhaolu and Maverick were DAC/Amps. I preferred to go separates. Even with those combos I used my heavily modded Creek OBH-11 amp (replaced all capacitors with boutique caps Nichicon/Elna Silmac and dual AD797s on BrownDog adapter for opamps).
4. Spend as much as you can stand/afford for the best sounding equipment. Go to a meet if you can and experience as much as you can. You can always put it up for sale on Head-Fi if it doesn't pass your sound test.
I had no experience with DIY stuff. I read through the forums and have learned one heck of a lot since last May. everyone has been terrific with assisting and sharing information.
Hope this helps, it is a very fun journey. Right now I am enjoying some HD Tracks through iMac/PM/iTunes>HiFace>Opus>Roc>HD650 SE. I hope to balance the HD650s in the near future. It is a very enjoyable listening experience 8^).
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Finest kind,
Chris