The only games I've double dipped with are TES:V Skyrim (originally had it only on PS3, but after seeing the huge modding community . . . well), Dark Souls 2 (Black Armor Edition on PS3, which had no DLC and then Scholar of the First Sin on PS4, which included all the DLC), Dragon's Dogma: Dark Arisen (originally only on PS3, but yearned for it on PC when it was re-released), Star Wars: Battlefront 2 (PS2 first and then PC) and Tom Clancy's Splinter Cell: Blacklist (Initially only on PC, but then bought it on PS3).
I really don't regret any of these purchases. The console version of Blacklist had local-coop support, which the PC version lacked. Dark Arisen's framerate was atrocious on consoles, and was magnificently eliminated on the much better PC release. Star Wars Battlefront 2 on PC has awesome mods, and similarly the PC version of Skyrim is far superior than its console counterpart. Pretty much if a feature was left out on one of the releases, and was present in another I repurchased accordingly.