I think comparing the cost of good to exceptional digital components vs. good to exceptional analog components is something to take note of.
I would think spending $5K to $6K on an analog system would get someone good to exceptional sound that will not be outclassed down the road 10-15 years.
But I think spending $5K to $6K on a digital system will only give good to exceptional sounding for 5 years at best ....before it will be outclassed and out performed by better chips and designed audio gear.
About 2005 the Benchmark DAC1 was a great DAC for about $1K. By 2011 Chord, Weiss, Audio Note, Cambridge Audio, Lampizator and many other companies came out with exceptional sound DACs.
The Chinese gear that is coming out now, I think ,is proving that quality digital sound is changing fast IMHO.