Re: GSG 1911 or Ruger P95
I suspect you got the GSG because you liked it. Do you like the P95? I cant say I'm a big fan, myself. It's also kinda clunky for a CCW piece. I have no idea on resale of the GSG, but Ruger resale sucks. By the way, I think Ruger makes fine guns and I've used a P89 and P95 quite a bit. They run just fine, but I don't care for single/double/decock guns, nor do I like the extreme front heaviness of the Ruger P series.
It's nice to have 22s in inventory for plinking and training newbies. If it were me, I'd hang onto the GSG and pick up a suitable CCW when I got my permit. In the meantime - start carrying ALL THE TIME at home, so you're already sick of carrying a fat, heavy, ugly pistol by the time you pick out a real CCW gun. That way, you're much more likely to choose something more practical, that you'll hang onto for a while. My first CCW gun was my XD45 5". It didnt bother me for 2-3 months...then I git sick of it fast, the novelty wore off, and I got a more reasonable CCW piece.
Hope this helps.