Reading your lists remind me of games I forgot:

Crazy Taxi, Street Fighter 4, Streets of Rage, Mighty Switch Force 1 and 2

Rings of Power on Sega Megadrive.
Bought my first copy at a second hand shop when I was 8, 21 years later and it's still my most favourite game of all time.
A few years ago I bought another copy which has the guide and map.

F-Zero GX
Wave Race: Blue Storm
Resident Evil 4
... and numerous games through Virtual Console

Mario 64/DS/n64/wii
Ocarina of time/64,GC,Wii,3ds
zelda 1, nes,3ds,gc
zelda 2, NES,3ds, GC
Mario bros, NES,3ds


probably some more just dont feel like thinking.

I bought Resident Evil 4 and Super Mario World so many times that I lost count. They are  in my top 10 so I  would buy them  once again if I could.

I rarely double dip. I bought GTA: san andreas twice. that was the only one.

Call Of Duty 4 - PS3 and PC
Monster hunter freedom unite - physical copy for PSP + digital copy for Vita.

GTA IV PS3, then GTA IV Complete edition again for PS3
GT5, then GT5 signature edition for PS3

I will probably get another copy of of ni no kuni since I dont want to open my wizards edition.

Off the top of my head:

Resident Evil 4 (Gamecube/Wii)
Super Mario 64 (N64/DS)
The Metroid Prime Trilogy - I had 1 and 2 on the Gamecube. I had 3 on the Wii. Then I had to get the Trilogy when it came out on the Wii.

IF PS1 on PSN counts them the list is giant, main culprit being Blood Omen : Legacy of Kain and FF VII to IX.
If we can count the HD collections most of the PS2 games re-released on PS3.

I don't think you have a problem unless too much disposable income could be considered a problem for someone.

Well, yeah... I have bought Halo CE at least three times and will have bought it four times with MCC :). Also, the sonic series have been bought in full on MegaDrive, Saturn, 360 and some of them on Vita as well. Ikaruga I owned on both Dreamcast and 360 and Guardian Heroes on Saturn and 360 There are probably dozens more :).