>>42870670First was Red (recieved as a gift)
Skipped gen 2
Traded a Yugioh GBA game for Sapphire
Bought Emerald preowned
Received Pearl as a gift
Bought Platinum
Played White, Black 2 and Soul Silver on a flashcart
Bought Moon
Got lucky with US/UM and SW/SH. My local game store ran a preorder deal where if you traded in a game worth more than $20, you could preorder one of the new pokemon games for less than half price. Both times they fucked up and sold me both versions at the discounted price on release because their employees somehow didn't mark the preorder as having been fulfilled or something (idk how their system works).
tldr got US,UM, Sw and Sh for about 80% of the full price of a single version of each.