When my laptop's shortcomings start annoying my too much, I start looking at new ones. It usually takes me another 6 months or so until I'm comfortable enough with my money situation to drop the cash.
Last time, it was the single-core processor (too slow) and parallel ATA (not enough options) that got me looking for a replacement for my Thinkpad T43p. This time, my E6400 has an overheating problem and Dell refuses to get back to me with how a quote for an upgrade to onsite support (and I can't be without my laptop for the amount of time it would take for them to fix the problem, especially because this is a well-known problem with the E6400 that they haven't figured out how to fix).
I think I might get a Mac this time around. New Macbook Pros are supposedly coming out sometime soon, and now that they have DisplayPort, I can get a DisplayPort splitter to run two monitors off one port. And I've kind of been tempted by MacOS for a while now.