It makes sense to me. Even assuming the high cost system is completely synergized it's possible and reasonable for someone to prefer a less refined sound. The key is that he enjoys his listening experience.
As a rhetorical question - what's the difference between a $1,000 system, a $10,000 system and a $100,000 system? The cheapest system could actually sound pretty decent, especially if purchased used. The middle system will be clearly better in every area and will be capable of very high quality sound reproduction. The expensive system will perform better than the middle system in certain areas, but the difference between it and the middle system is less than that of the middle system and the cheapest system.
I frequently read posts where "the journey" aspect of this hobby is invoked. This person's journey deserves as much respect as any other. And as a point of reference his mid-fi system isn't all that mid-fi.