That's a good point about lossless and lossy compression.
The real question becomes are you trying to convert vector into raster, or not. If you are, you do lose some information in the process, because vectors are always approximated by raster. While raster regions can have inside and outside topology that is converted into vector polygon of different topology inside and outside, you don't have direction. Vector back to raster you lose the direction of drawing of vectors if they go from point A to point B.
If you did a pure postscript print job, you'll likely gain more information than PDF to postscript or vice versa. A software called Ghostscript I've heard has a much better rendering of postscript prepress than just PDF. Though I've never tried it myself.
http://pages.cs.wisc.edu/~ghost/