Got my 20D for I think about $1100 new. Dell had some screwey screw-up that let me combine multiple coupon codes and I jumped on it. They were closer to $1,500ish at the time. And this was within a few months of the 20D coming out.
Best deal was back in the 90's, when I bought a new Canon EOS 10s for $450 and a 80-200 f2.8L for $1100 (it was great when non pro cameras were still sold at CPS prices!!). i sold both over 5 years later and got around $500 for the 10s and what i paid for the 80-200 f2.8L when i upgraded to the 70-200 f2.8L. On the flip side, i took a big hit when i upgraded from the 70-200 f2.8L for the 70-200 f2.8L IS.
Last year i bought a new 85L II for $1750 CDN (after CPS and the instant rebate) the lens now retails for over $2400 CDN. So I suppose if I was overcome with insanity and wanted to sell my 85L, i might make a profit on it
Bought a used Bronica SQ with grip, 80mm and 120 back for 995 in 1985. Used it professionally for 20 years, sold it for just under half that. The body never let me down once or required any servicing. Was a good deal.
There are deals some people seem to have got that go well beyond sweet........they are unbelievable.
It would be interesting to hear from a real pro as well, someone like Voodoo, etc.
I read somewhere that the worst nightmare for a photographer is that in the event of his sudden demise, his wife would sell his gear for what he told her he paid for it.
this is minor deal 40 D 4K clicks (nobody wanted to buy for $ 750 in sep 08 )traded for mint , clean as can be 70 -200 f/4 IS and 1DMkIIn with 10K clicks mint cost me $500 after I sold my 30D +grip for $650 LOVE !!!!! 1D MkIIN with 70-200f/4IS
So far this year's deals include a Caltar II N 300mm in excellent shape for $275 from Calumet ebay. But the best deal I've gotten was a mint 1Ds with 4328 clicks for $300 cash and an over under shotgun from Turkey I bought in 2000 for $400. No complaints here.
Years ago got 3 Bogen 3001 tripods with pan/tilt heads for $30 apiece, Nature Company store going out of business. My local camera store gave me a dirty but fully functional Domke F-2 that came in on a trade, and sold me a used Canon 220EX flash for $40, good people.
Went to a local estate auction for a doctor that was also a wildlife photographer with evidently a buying problem. He had soooo much equipment and most of it was brand new in the boxes. There were very few people at the auction that even new what the stuff was and didn't bid very high. The auctioner started to ask me what to start the items at. I got so many items there and then just sold off the things I didn't want/need. Ended up with several nice Gitzo tripods with Arca Swiss ball heads and 3 white lightning strobes and Sekonic meter amoung many other items. I just didn't have enough liquid funds to keep buying! On one of the lots with some Nikon flashes I bought to resell there was a little Zeiss lens that looked like a microscope optic-turned out to be a semi rare lens for macro and it sold for $475! I also had a great deal in the 90's on some used Bronica equipment that I basically got the stuff I wanted for free after selling the extra pieces, but the auction really takes the cake for me. Sure glad I didn't have a wedding that day!
I usually buy things at fair, reasonable prices, but I couldn't think of a single "steal" to compare with all the stories here without going back way before digital.
I found a Leica IIIc in a small town camera store. The owner was selling it for $150 with a collapsible 50mm Elmar in mint condition. I never liked the camera much, so I sold it for $110 (to a dealer, no less). I still have the Elmar. For a net price of $40, I figure it was a bargain. I also got the adapter for Leica screw mount to M bayonet for $5. I haven't checked on those lately, but they used to be hard to find (at least the original Leica manufactured version) and a bit costly. That's about it for me. What a poor shopper!