Heh, congrats. I think for the low price of the Clip+ you don't have to be ashamed in front of your wife. Not to mention you know you'll have a player that sounds better than the Hifiman.
Not sure what you usually do, with your other players, but I simply drag'n'drop stuff over, I don't use any sync-apps, media players, and whatnot. The most important thing is setting the Clip to MSC mode in its system settings, not Auto or MTP. That way it acts like a normal USB flash memory stick.
To get the most out of the Clip, making it the best player ever, there's Rockbox:
http://anythingbutipod.com/forum/showthread.php?t=53702 But maybe you want to give the stock firmware a whirl before you mod it? Either way, I only use Rockbox on my Clip+, and I've stopped using all other players on the go.