Foobar2000. While it is customizable, you don't have to do any of that, so don't be scared off. I have done virtually nothing except make the play/pause button on my keyboard go to Foobar for convenience.
My favorites from the linked list are Russian Circles "Enter" and Red Sparowes "Every Red Heart Shines Toward The Red Sun". Neither have vocals. The former's a bit heavier. Really besides Tortoise and Stereolab I haven't heard much from that list, so I'll have to do some research as well! I second Pelican as well.
This might not help, but you probably cannot be proved wrong. I also think you've listed most of the competitors. I've not heard of Laika or Archive but like all the rest. It's not a huge genre. Maybe try Goldfrapp "Felt Mountain"? Looking at the music map I can say I very much enjoy Air, which isn't really trip-hop but is closest on the map. I also like Thievery Corporation.
All of it or just the new stuff? Do you like Opeth? For The Sword you should start with one of their latest two. I find genre-labeling hard and confusing for the most part. What sort of musical qualities are you looking for most here?
I like your list, but I'm not sure I'd categorize The Sword that way (though I love them). I think they're more stoner, less prog. Great if you like riffs. Maybe look into Intronaut, Burst, Anciients, New Keepers of the Water Towers' latest. Though it's more post than prog, Russian Circles' sound is dark and heavy IMO.
I would say there's no reason not to rip to lossless (FLAC for me) for my main/permanent collection. However, I also create a -V3 mp3 at the same time for my portable. Fitting a good deal of music on a 32 Gb SD card for my Clip+ is great, and lossless isn't going to do **** for my van's factory speakers or my KSC-75's while throwing some iron around. For posters that have 1000's of CDs I can see where the space would add up, but I figure I'm at the high end with 650+...
I'd have to say I grew back into it. I sort of liked the heavier stuff in high school (hair bands, grunge, etc), but didn't really have access to much more in small-town Iowa. In college I spent a lot of time "chilling" and listening to more trip-hop and electronic, but after that I realized it wasn't really my favorite normally. I started getting back to the heavier stuff and eventually grew to like a wide range of metal, and now it's pretty much all I listen to. I'm...