Worst deal was on one of the first pins I bought: Xenon... the face had been repainted BAD (one eye was bigger than thge other, mouth all wrong...) front glass was missing, electronics were a basket case... generally a wreck... paid £500 ($800), bought a replacement playfield for it that was also not great for another £150, and a smoked glass for around £50 (total now £700, $1100)... Ended up selling the game non-working for £500 after finding a better example... This left a bit of a bad taste in my mouth for pinball (I was hustled by the seller to be honest), and in an attempt to get rid of this bad taste, I started buying pins that were a good deal in order to sell for some profit to recover the loss on the Xenon... I kind of overshot a bit...
Anyway, best deal was Williams 4 Stars that I got for a crate of beer... not in bad shape either...