my how i've had many finds over the years
One significant haul that got my off and collecting was a video store that went under. They had EVERYTHING up through PS1, but i was a poor kid just outta high school. I ended up snagging 300+ CIB NES games for $211.00... i still have the original check back i wrote out for that one somewhere...
After that, bought out three more rental stores, one for $300 and the other for $1k. At that point i almost had a complete CIB NES NTSC set, including all of the known (at the time) color dream variations complete.
Some of the stellar scores in the mix:
FFF Athletic world -$10 shipped - ebay - before anyone knew about it

, sold it to Dain as he was a smart smart man when i was selling out.
SE Manual and FFF Pad - $265ish or so (can't recall) - ebay
Cheetahman II - $125 ebay
Caltron box/manual/sleeve - $10
Myriad box/manual - $10
and that's just NES wise. I have found some of the hardest to find A800 and C64 game cartridges/disks (complete ones too) in the wild and for next to nothing. I've made some good good money on video games over the years and will always be grateful for this hobby.
Now i pretty much pay market value on stuff as I don't have the hunt in me as I used to... but i still always love a good deal