Ratchet & Clank 2 & 3 (owned them on PS2, bought the HD collection for PS3)
Sly Cooper 2 & 3 (same as above)
Jak and Daxter: The Precursor Legacy (same as above)
Skyrim (Bought it on PS3 2 years after launch (so it actually worked almost bug-free! 
), bought it dirt cheap in a Steam sale later as well.)
Ratchet & Clank: Into the Nexus (bought it digitally at first, because my retailer didn't take any copies into stock =_=, regretted and bought the physical edition later)
Geometry Dash (bought it on iOS first, after playing through the free trial (which was surprisingly content rich), showed it to many of my friends, many of which also bought it, but then I bought it again when it got a Steam release)
I've yet to buy a game more than two times.
