Hmm, back on site and having recovered from my previous spending spree , and am again interested in getting an imod or HM-602 (i prefer imod though) with the required LOD. Holding off on the P51-mustang. (just missed out on an imod for sale on head -fi due to not being on this site regularly enough, and it was an in Japan seller too, grr)

i've been using MAX, Tag, and Play by sbooth.org with very good results. MAX is one of the better cd rippers on the mac. It can also do the CDparanoia and error checking as well as rip to a number of different formats all at one go. Tag & Play are just what the names suggest. Tag is a tag/metadata editor and play is a simple player.
 
An alternate to iTunes (if you're library is mainly a format iTunes "doesn't do") is Songbird (by the Mozilla group, same people that make the wonderful Firefox & Thunderbird) if you haven't figured... i'm a big fan/supporter of open source projects.
 
I have a 5g video as well and have been debating the diy-mod.
Started out with a used 30gig 5g, grabbed some parts from demigods (back, switch/jack, hd bumpers) and the HD/battery upgrade from apricorn. so now it's a 240gb 5g Video. i did my research and chose a used 5g video mainly for the space w/hd upgrade. i'm too indecisive to pick a small section of my library to throw on a SD card.