I'd suggest to drop the traditional speakers altogether and start using headphones. The industry standard Sennheiser HD650 or Audio Technica M50 will bring more sound quality for the buck from any loudspeaker I can think of. Of course, this is just an uneducated suggestion. Maybe you love to share your music.

He might work from home or in a private office, or these might just be for a home setup. I have AKG K550s for the office (I know I'm paying for the fact that they're closed) but bookshelves, a small amp, and a DAC for home.

As comfortable and great as these headphones are, wearing them still fatigues me and I just don't enjoy having them on. I really enjoy speakers.

In my college dorm, I had TCA WAF-1s with a TCA Gizmo. I've upgraded my amp and purchased an inexpensive DAC + Energy 12" sub since then, but I'm very happy. You can spend a few hundred and have a really nice setup; after that point, you'll see marginal improvements but with huge leaps in prices.

Wearing AKG K550s do not cause any fatigue for me. Well, I guess one has to try before going all in on headphones. I personally don't like the sound from loudspeakers. Well there are some setups that I like but I have neither the budget nor the suitable place =)

By the way, don't your k550s also leak? However I adjust the pads, it still feels like everyone could hear what I'm listening. Never tested them by making someone else wear them but they feel not tight enough so never bothered to bring them to the workplace. I'm working in a shared office, so it really matters. Currently I'm using my M50s but k550s are so much better and if it's not as bad as I thought, I'd definitely use them instead.

I have a truly large head, so it's not really a problem for me. When I was reading reviews, there were plenty of warnings about improper sealing if you didn't have a large / certain shape head.

There's a decent noise floor in my office, and most of the other people use headphones. Even for the ones that don't, there's enough that my music isn't really audible. I'm also pretty vigilant about keeping my volume low, mostly for my own health.

I have HD 485s, but even at the loosest setting I can't wear them for more than 30 minutes because of the way they feel on the tips of my ears.

Well, I don't want to sound condescending but the headphones I'm recommending are both priced well above HD485, apart from being highly appreciated (mostly) in the audiophile community. Also, HD650 is known to be very comfortable and having 15 headphones to compare, I can tell you that you can go for it without a second thought. It's a very nice investment for one's ears =)

I have tritton 720+ and they also hurt my ears after a while. It is because they put the sliding part to low, so it minimaly adjusts the width. (probably to maximise the ear/top of head proportion) Or I have sensitive parts near my ears?

Tritton 700 series are pretty decent for gaming. However, gaming headsets aren't designed for long term listening. Maybe you can consider getting something like Beyerdynamics DT990 Pros as an all-round headphone for daily use.

AudioEngine A2+ - $249, active, with integrated USB DAC. Really nice. http://www.amazon.com/Audioengine-A2-Premium-Powered-Speaker...

Usually pair with DS1 stands (just enough to tilt off the desk and towards your ear), $29 http://www.amazon.com/Audioengine-DS1-Desktop-Stand-Pair/dp/...

and things will sound good.

What is your definition of good desktop speakers and price? In the UK we can get this sort of thing:

http://www.richersounds.com/product/standmount-speakers/camb...

Which are great desktop speakers at £80GBP

Nothing like this in your neck of the woods?

It should be pointed out that these are active speakers with a builtin USB DAC. There are a variety of these things out there at this price range atm and they sound surprisingly good. Recommended.

Alternatives:

http://www.thomann.de/gb/alesis_m1_active_320_usb.htm

http://www.sweetwater.com/store/detail/StuDock3i/?adpos=1t1

(There's a decent chance all 3 are the same product rebranded tbh.)

For price-worthy PC Speakers I recommend Teufel: http://www.teufel.de/pc/pc-stereo21.html

I am also very satisfied with these headphones: http://www.thomann.de/de/beyerdynamic_dt990pro.htm The sound is crystal-clear and due to the big and soft earpieces you can wear them for hours without noticing. Perfect for home use.

If I had my time again with headphones, I'd be buying DT770 (work) / DT990 (home)/ Bose QC15 (travel)

The Beyer's are very comfortable which I think is the #1 feature for long periods of use.

The Bose make my daily commute enjoyable now as I can listen to podcasts with no distraction.

Soundsticks? http://www.amazon.com/Harman-Kardon-Soundsticks-III-Multimed...

I'm using these at home too.

Previously I went through Logitech's every 2-3 years, I've never even considered changing to something else since owning them.

I've had those speakers since 2005, amazingly good hardware.

I concur. Not only is the sound surprisingly good for the price, but they look pretty cool too.