Thijazi, interesting journey. I share an almost similar upgrade path, starting with the NAC 202 / NAP 200 but settled with the NAC 282 / Hicap DR / NAP 250 DR. Although the NAC202/NAP200 replaced costlier amps in my system(Audio Research preamp and Plinius Class A power amp), the Naim amps gave me higher levels of listening pleasure. I thoroughly enjoyed these amps for a good 5 to 6 years before going up the ladder. I still retain the NAC202 and NAP200 for a second system although I now have NAC282 / NAP250DR in my primary system.
It must be a very huge jump or improvement going from the NAC 282 to the NAC 552. I agree that every step of the upgrade will yield sonic improvements. Small or big they are equally enjoyable.
Enjoy the music.
Ryder - further to the questions you asked me about the 252 and then the 250DR v 300DR, looking at your post here where you describe your system, I think I'd be inclined to try a SuperCap before thinking about upgrading your 250DR to 300DR. When I demo'ed the 282/250.2 it took me about ten seconds of listening to the SC power the 282 as compared to the HC to decide I had to have a SC. The soundstage just expanded beautifully. In my view the 282 is capable of a wonderful performance when powered by a SC.