Wine has been able to install Outlive for me just fine. The problem is that after when I run Outlive I go to "Single Player" and it asks me to insert a CD drive which is already inserted. I have run:
You are missing the symlink to the device, ~/.wine/dosdevices/d::. But why are you creating these manually? Running winecfg with the cd mounted and clicking Autodetect should work.
The most common reason for that problem is copy protection. Some games will not work in Wine without a no-cd patch. That's something you would have to find and apply on your own; helping you with that is against forum rules.
You didn't mention what Wine version you're using. If it's not the latest development release, try upgrading before you try anything else.