I don't think your ICON player can output anything more than a 16/44 signal, so a lot of your questions might not be applicable just using that transport. Some DACS can "upsample" that signal to higher levels; I have ultimately found that to be a mixed bag, as it adds a bit of noise to the playback. I can tell you that, in my view, the higher-resolution sources, be they 24/96 or 192 via a download or SACD, do sound better than a standard 16/44 CD, closer to (but certainly not the same as) your analog setup. The differences are more subtle, IMO, in that they just make the music sound more like a real event than a reproduction--I'm sure you probably have that feeling listening to vinyl vs. CD. You won't be able to get SACD playback from your current setup; you'd need a transport that can read an SACD and a DAC that will accept and convert the DSD signal; the standard CD signal is PCM encoded, a different system.
For computer audio questions, which may ultimately be the best way to go, you'll need to look elsewhere than me for any specific advice. I can tell you that my Memory Player (which essentially is a computer) does sound significantly better playing a CD from its memory than the same CD played on a very high quality transport (using the same DAC), and I'm sure from having heard good computer setups out there that they can make the same claim. It also is quite convenient, you'll see if a friend of yours has a good computer setup just how easy it is to store, organize and play back music files. You won't have that tactile feeling of putting a record on the turntable/CD in the drawer, but I'm very impressed with what a lot of these computer-based systems bring to the table.
For computer audio questions, which may ultimately be the best way to go, you'll need to look elsewhere than me for any specific advice. I can tell you that my Memory Player (which essentially is a computer) does sound significantly better playing a CD from its memory than the same CD played on a very high quality transport (using the same DAC), and I'm sure from having heard good computer setups out there that they can make the same claim. It also is quite convenient, you'll see if a friend of yours has a good computer setup just how easy it is to store, organize and play back music files. You won't have that tactile feeling of putting a record on the turntable/CD in the drawer, but I'm very impressed with what a lot of these computer-based systems bring to the table.