It's tough for me....I was a HUGE Syd fan in HS and a little beyond, only liking Animals and WYWH past "Meddle."
However, that said, the music put to regular album was a little less free than things I heard on bootlegs. Hearing Astronomy Domine and Interstellar Overdrive on a few boots, even if cut off versions, gave me a slight insight to what it must have been like to see them live. THAT's what I like best....
As for Roger Waters, I don't doubt his genius/talent, but the music of The Wall and beyond just wasn't for me. Personal taste thing; didn't like his solo work either.
David Gilmour to me has some of the most expressive guitar work, and I like what he's done, with PF and solo.
But ultimately, my rankings would probably be:
1 - Piper At The Gates Of Dawn
2 - Meddle (solely for Echoes, but I don't get tired of One Of These Days)
3 - select songs from Pulse (especially Astronomy Domine, played SO much better than on UmmaGumma)
4 - Animal or Wish You Were Here, tied.