infyrin: It's not necessarily an obsession. It's a concern. Being concerned doesn't constitute having an obsession. For all I know, it could help clarify a matter so that way it is known to people who might see to abusing it, giving them something to second guess or maybe it'll let people know about where Steam or GOG stands on the matter.
Now what I don't understand is having two copies of the same game in two different places as two different versions - DRM-Free and DRM-With. I'd like to manage things the way I want to, if a game I remotely like is best left on Steam for obvious reasons - it stays on Steam. If I want a game on GOG for all intents and purposes, a back up I can play or something I can enjoy without the need of it a program to run, then I may want that game on that side.
Since you explained, then I have to give my answer. Whether you like it or not, I can assure you my answer is correct in everything, except when GOG themselves correct me.
Let's take example of Witcher 2.
You have it on Steam, and use GOG connect to redeem on GOG. You download GOG copy and delete Steam copy (through Steam's self support).
GOG then realize you no longer have it on Steam and remove your copy of Witcher 2 here.
Guess what, you are INELIGIBLE to play that Witcher 2 anymore. Your license to play it legitimately is gone. If you install it for whatever reason, you are pirate.
Just because it's DRM free doesn't mean you can do as you please legally.