Help me - am I stupid

Well guys - I am a vinyl man - but am getting sick and tired of the continuous price hikes for every decreasing quality of LP's - so I bought a decent CD player that had the DAC input option - it's a cayin CDs 55T.
One of my other questions that both the guys who have answered may probably help with is this?

1. I get High res if the original recording was in high res, or if taken of master tape in high res - but what is the point in upsampling?
2. How do we know what resolution something was recorded in in the first place?
3. any point in going above 96 KHZ

@mzkmxcvasas 
as to the 10 second thing - I think we are at cross purposes. Simply put there are certain cues in analogue that I find red-book just does not do so as to make the music listenable - it never truly feels relaxed. 
I always wonder if cd has lower res than analogue - or is it the opposite - is it something else?
Al said and done my Cayin CS 55 CD is a very musical listen - 

Funny thing I find with Digital vs analogue is that with Digital you keep listening albums end to end whereas with digital you seem to skip - and its not just a matter of ease of skipping.
I went to a fascinating talk by the Editor of Stereo magazine at lat years high end show and he said its like the darkening of seismographs that always thicken and darken on a shift - the same occurs with the styli' going through digitally mastered grooves.
the few times I have heard high res I have found it much better than 44.1.
My point is that I find differences show over longer listens (lol - making my excuses early)