First thoughts: Ripping files from CDs in their full format is taking up a lot of room! Good thing prices are continously dropping on storage.
I have a Clip Zip purchased from Radioshack for ~$30 (Rockbox) and an E6 purchased from Amazon for about the same. They're pumping sound out to a pair of M50s with no more than 30 hours on them (straight cable variant, $105 Amazon). Your typical starter rig for sure. So far I've ripped the clip off the Zip and sanded down the leftovers to make for something nice and compact. When I can post pictures, I will. Pretty impressed with this new world of music so far!
Future plans include picking up a used 160GB iPod Classic and Rockboxing it along with an E11/LOD combo. I'll keep my mini rig and pick up a decent set of IEMs for gym/walking/grilling/i-dont-want-to-carry-all-this-and-wear-cans use
EDIT: I have fairly large hands, so something about the size of an iPod is perfect for me, as are the physical controls. I can entirely hide the E6 and amp in my fist =)
Edited by southerntide - 5/30/13 at 11:20am