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headphones + amp for $400

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Tube amplifiers color the sound and have bad characteristics when combined with with low impedance headphones. Generally do not buy them unless you have a combination where you think the sound quality is superior. Normal solid state amplifiers are much better in every aspect.
 
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What would be the best desktop setup if I wanted to test the waters (IE lowest price). Something that will motivate me into investing in a setup close to $1000 in the future.

I listen to all sorts of music. I love bass, but it doesn't have to be loud base, just crisp and clear. I also play games, mostly FPS and Eve Online, etc...

If there is a portable setup that could do the trick, that will work also, I just figured a desktop would perform better at a lower price.

There is a portable fiio amplifier, and while I read that their quality isn't really up to snuff, it is still an amp that has generally good reviews. I just wonder what a $30 amp can really do.
 
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System Name Ultrabeast GX2
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Audio Device(s) 7.1 Digital on-board, 5.1 digital hooked up
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Software winXP Pro
Benchmark Scores 17749 3DM06
I also enjoy the classic look of the tube.
 
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I think the O2 + oDAC is the way to go or possibly the new desktop version of the O2 which is due out shortly. With regards to headphones I think the cheapest way to get something really good is the Sennheiser HD580 they are very cheap used and you can get spare parts for them from Sennheiser. That is probably a $400 setup. I would not recommend FiiO they are obsolete designs.
 
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Location
Joplin, Mo
System Name Ultrabeast GX2
Processor Intel Core 2 Duo E8500 @ 4.0GHZ 24/7
Motherboard Gigabit P35-DS3L
Cooling Rosewill RX24, Dual Slot Vid, Fan control
Memory 2x1gb 1066mhz@850MHZ DDR2
Video Card(s) 9800GX2 @ 690/1040
Storage 750/250/250/200 all WD 7200
Display(s) 24" DCLCD 2ms 1200p
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Audio Device(s) 7.1 Digital on-board, 5.1 digital hooked up
Power Supply 700W RAIDMAXXX SLI
Software winXP Pro
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There are some 595s for $110, though the used 580s are $200 minimum used. There is not a whole lot of used stock either.
 
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Processor i5-2500K
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Case Lian-Li
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Power Supply 600 Watt Corsair
Software W7
Check head-fi.org they usually go for around $140ish.