I was reading through some of the blogs off of newsdot, and came across mewse talking about the lure of cheap computer books. I know this feeling too well — in the center of Bristol there are a couple of bookshops that are often selling computer books cheap, and I always end up browsing through them all. It's worth it sometimes, though: I got a copy of Python Essential Reference for £8 last year (RRP £25).
The best deal I ever got was when they were clearing a lot of Java books. I got Just Java 1.2 for £8. Genuine official Sun Java books for under a tenner!
Worst purchase: well, apart from all the ones I haven't even got around to reading, there was Web Application Development with PHP4. Admittedly it's not the author's fault that PHP is utter rubbish, but the book basically spends its whole time telling you how to avoid making all the mistakes that PHP makes it so easy to make.