Well, let's see....
I bought a laptop for school work, but I always ended up doing everything on my desktop.
I bought an ipod video 60gig, and I thought I would watch movies on it and listen to music, but the battery doesn't last long enough to watch video, screen is too small, it doesn't play many movie formats, and I rarely listen to music. On top of this, itunes must be the worst software ever for music xfer. Every time I have to use it I have to learn it all over again. It's a friggin' nightmare. All I want is to put some songs on my damn ipod, but itunes starts bsing me about these... libraries and stuff. I don't want any damn libraries, just let me click and drag songs damnit!
I end up using my ancient RioS30S more than my ipod. I'd like to sell this thing, but having paid $400 for it, $100 is just not good enough since it's in perfect condition.
Got a PSP because I thought I'd be playing emulators and games on it, but somehow the controls are horrible. The analog stick is very unresponsive and games get boring quickly. Playing mario and sonic from SEGA and SNES days was fun for about 5 minutes... GTA Chinatown wars got boring in about 2 minutes as soon as I realized it's impossible to control cars... I thought Fighting Games would be awesome on the go, but PSP's controls are really not designed for fighting games.
My PS2 suffers from the same problem. The damn analog sticks.. Who thought of these when there's D-Pad? analog sticks are too sensitive and imprecise, and hence, control becomes a nightmare...
Bought a SFIV TE stick to play SFIV on my PC some time ago. I thought it would make me an uber SFIV/KOF player. Heh.. Little did I know.. $150 down the drain...
My Blackberry Bold doesn't get much use either because I'm too cheap to pay internet fees and texting fees.
Now I am thinking about the ipod touch, Xbox 360 or a PS3. But really, I bet I'm not going to listen to music on the ipod, and watching videos will be a chore. Most apps are useless too. And the consoles will probably sit there collecting dust just like the PS2...