Ok, on second glance, there's something odd about that error. Could you run it again but with aptitude instead of apt-get? It usually returns more useful messages.

Nothing is safe. From what officials do you need approval?
Let's put it this way: depends on what you want to run. Some old software runs fine with the ancient wine version provided by Jessie. Most modern ones just won't. And, if you show up at winehq asking for help, the first advice you'll get is to update to latest version.

Which GPU and driver do you use and how did you install the driver?