As far as high priced analog, it has been my own personal experience that you can definitely better CD with good analog, but you have to spend much more to do so. I realize this may have to do with poor matching, or bad synergy, so this is not to be taken as an absolute statement. I have a relatively entry level turntable setup: Rega P2 with RB250 arm and Grado silver cartridge. I bought it used for $350 bucks. In the same system I have a Sony SCD-CE775 that I bought used for 175 bucks.
The Sony at least matches the Rega as far as redbook playback goes. Of course it is recording sensitive, but more CDs sounds better than LPs sound better.
My brother has a no holds barred Teres setup that sounds glorious; there are recordings that sound better on my SCD-1, but more recordings sound better on his TT than recording that sound better on my CD player. However his turntable setup cost a helluva lot more than my CD player.
Now if you compare SACD to the vinyl, there is no comparison at the same price point. I couldn't tell you whether a 10k digital SACD setup sounds better than a 10k TT rig, because I have never heard a 10k digital setup. But I do know that at the entry level of both, SACD sounds better. My cheap little Sony playing back SACD surely has some glare, ill defined bass and lightened highs, but those weaknesses are not as pronounced as the weaknesses in my TT.
But I do know that my 3k SACD play rivals my brother's 13k TT setup. It may not be better, but it is damn close. 10k is a lot to pay for something that is only sometimes marginally better.
I realize software is another issue altogether, but I am just talking about analog prices here.
Has anyone else noticed this, or am I just goofy?