Quality system, make poor recordings sound better?


I notice that as I move up the audio chain, poor CD recordings sound worse and the good ones sound superb, should this be the case? Also I on any given day my system sounds different even with the same CDs. Any thoughts on this as well?
phd
11-07-14: Metman
there's some very good and interesting responses here but it would be nice if there were a few paragraph breaks for some of the longer ones.

Some folks do like to Ramble On. ;^)
11-07-14: Rodman99999
The Dreamboat Annie masters were excellent. Nautilus did what I think was the best pressing of that album. Still my go-to for demoing Rock bass resolution(the synth & drum/Fender bass doubling on Magic Man)
How about the CD? I'll pick one up if also excellent.
11-07-14: Whart
Knight- Dreamboat Annie on Mushroom records, which I think is a KenDun master is actually a great sounding record.
I have most Heart but no Dreamboat Annie :-) There are hi-res releases now so quality has improved?? Concerts in Blu_Ray is very good.
Knight, sorry, don't know about the digital versions. I 'rediscovered' this piece of vinyl a few years ago, and was amazed at how good it sounded. Looking it up, it was apparently a 'demo quality' record in its day. (I was around in that 'day' and certainly remember the songs from the radio, but it wasn't on my radar for home listening). Mushroom was a Canadian label, i think, and these may be earlier pressings, but I believe they were widely distributed at the time~ doubt it is an expensive record if you do vinyl.
Enjoy.
Katy lied by steely dan is a great example concerning this thread. I have always liked Steely dan and heard many times that album has problems. I just didnt understand until recently.

I can only come to the conclusion, the resolution of my system is now revealing the weakness or issues.
Oilmanmojo

Very interesting as Katy Lied has a couple of my favorite Steely Dan songs. I haven't listened to it except on my ipod in the last...actually I can't remember the last time U sat and listened closely to it. Makes me wonder if my system as is will reveal the flaws.