I've made a LOT more money on pedals that I paid for them. About 6 years ago, I decided to get rid of my old pedals and start getting some of the new technology (boutique pedals).
I got serious about playing in the late 60's so had quite a collection of old pedals. I wasn't too informed at the time about the whole "vintage" thing.
I remember I first decided to get rid of my old EH Big Muff. I think I put it on eBay for about $25 hoping to get a few bucks for it (along with the rest of my old "junk") so I could buy the new pedals I wanted. Low and behold, the final bid was $300!!! I couldn't believe it. I even emailed the buyer to make sure he didn't make a mistake. He told me that my EH Big Muff is exactly what he had been wanting.
Anyway, I happily took the $300 and bought my first BJFE, the Honey Bee, for about $250. I sold off the rest of my old pedals with similar shocking results and have since bought many nice pedals to replace the old.
I have never understood the fascination with "vintage" pedals. I've owned (and sold) most of what was available "in the day" and it is pure crap compared to what we have on our pedalboards today.
I did get lucky, though, in that I got into the whole BJFE thing early on. I don't think I paid more than $250 for any of them. The mistake I made was selling off my PPF thinking that it just wasn't different enough than all the rest of the BJFE pedals I had. I really wish I never made that mistake. There is nothing like the PPF and now they are $550 and up (I think I got mine for under $200).
I also sold a 1963 Strat that I bought in 1973 (I think I paid about $150 for it). The amount I got for that Strat paid for my Suhr Custom Classic, 1958 Les Paul Historic Reissue, and a new boutique amp. Everyone that bought my "old" stuff was as happy with their new toys as I was to get rid of them to move on to the new