Help Recommend a Good System for $2000.

Are you at all comfortable with DIY projects? If so, I'd suggest making the cables. Making your own version of the Kimber braided IC's is really easy, and the DIY extension cord speaker cable (from Lowe's, Home Depot, or even Walmart) is even easier. If you're not into that idea, then just start him out with Blue Jeans Cable. It'll leave a much larger chunk of the budget for quality gear than almost any other product out there, and won't be completely outclassed by gear in this price range.

As far as components go, you might find that a Peachtree integrated would be a good choice as the built-in DAC is excellent, and it would allow for a computer source via the usb input. I would recommend reasonably efficient speakers (>=90db) as the power amp isn't very stout (in the iDecco I use). The main complaints about these things have concerned the power amp, but you should know that it's not suffering from the usual class D issues. It's grain-free with a nice tonal balance - just not the last word in resolution or dynamics. If you went for the Nova instead of the Decco, you'd have a better power amp and more flexibility for inputs. The other great thing is that if he decides to keep upgrading, the Peachtree makes a really nice preamp and headphone amp, just a DAC, or an all-in-one second system further down the line.

If you're wanting to go in a completely different direction, let me suggest a loudspeaker. Look for the Martin Logan Aerius or Aerius i. These definitely thrive off of significantly more power than the Peachtree can provide, but they're brilliant speakers. With the right amplification, I really think you'd have to spend a ton more to beat them. They should be 8-900 used (maybe $1000 with shipping if you can find any locally). I really can't recommend these highly enough. You can probably find a used Adcom 5500 or B&K EX4420 for < $400 that would be a nice match.

You might take a look at the Virtual Systems here on Audiogon, specifically the Budget Minded area to get ideas.

I'd do a mix of new and used equipment:

Tekton M-Lore at $650.00
Jolida Fx10, Sophia Baby, LM, Almarro 205, and similar $500.00 or less new/used
Grant, Shiit or similar DACs $350.00 +/-
Used transport Sony S9000ES, SACD/DVD/CD player or similar $195.00
JW interconnect and speaker cables $60.00 plus

I don't know where my original post went so I'll repost:
A mix of new and used, used easily found here on the Audiogon.

Tekton M-Lore ( StereoMojo Major Mojo award) $650.00
Tube integrated Jolida FX10, Sophia Baby, MiniMax, Almarro 205, all can be had from $350-$675.
Grant Fidelity DAC or Schiit DAC $350.00
Used Sony DVP S 9000ES as transport $195.00
Cabling and Interconnect JW Audio

Or you could swing for Audioconnection system which is also a superb set-up at a bargain price.

Full range down to 38hz - there's no escaping the laws of physics, you need something kind of big. How about Revel F12s? Considering a sub at a later date might open up your options.

In terms of front-end, not clear if you're looking for a Blu-Ray player, a 2 Channel DAC, or a streamer. They're aren't many units that do all things. The Cambridge NP-30 might be worth a look for a streamer/DAC, plus a cheaper Blu-Ray player hooked up to it via coax or optical.

For cables, I really wouldn't go nuts. The usual suspects are Blue Jeans, Monoprice, and Supra. Check listings for bargains from the likes of Kimber, Audioquest, etc.

The last thing is...the room dimensions and speaker placement. Going longfield down the full length of that room would give pretty bad results. For optimal nearfield/midfield listening, you're going to have to move the couch up into the top third-ish.

So again, longer term perhaps, he'd have to be thinking about bass traps for all corners, panels for reflections from the sides, and the new space that would exist behind the couch to that rear window.