I have been in the live music space for 30 years. I have worked with over 250 bands. I am constantly around old and new systems and actually like hearing music on old system configurations from time to time. I own seven systems myself, most low cost, and really appreciate a twenty year old system that includes a NAD 3020, Kef 104, and Garrard turntable. Yes, there are better speakers today, but I love listening to the music as I originally heard it in analogue. The speakers sound great--like a great wine--better with each passing year.
Hands down, the best speakers are pro gear by ATC. They are allowing these to be sold to end users for the first time this decade and they are in use at over 1,000 pro studios. A true "reference" product, one of the most overused and abused terms in audio. Most audiophile products claim this, yet never are used in professional playback environments. I would check them out--they play all genres better than any other speaker--but have a very limited distribution here due to their commercial rather than consumer roots. I also like the classic British sound of Spendor, Harbeth and Tannoy--very stunning midrange over most other speakers--easy on the ears and will add up to many wonderful listening sessions. Canada has the best performance to value--Paradigm and PSB are wonderful budget minded products.
There are really great "nearfield soundstage" products now around the digital music space, and I really like the iMod iPod from Red Wine ($250), the Pure Audio docking station by Logitec ($100), the Blue Sky EXO active monitoring system ($200 at Guitar Center and it blows away everything) and Audioengine speakers ($350). Many of the old systems can't handle the new compressed listening requirements of the MP3 format, and these products really shine around the new formats.