[moparado]

Instead of spraying oil on the weather stripping which would seem to me it'll smear the glass i'd try cleaning the weather stripping best you can with window cleaner with the window completely down.
Squeaky clean the glass and then apply an automotive paste type wax inside and out on the glass.

 

[moparado]

Concur about oil...it is my understanding that silicone spray will not degrade any rubber/plastic trim.

It won't degrade the window seals but sooner or later will attract dust, rain dirt, etc.

 

[moparado]

I'd spray the upright window inside and out with ordinary window cleaner then run the window up and down a few times.
Don't over do the glass cleaner.
Wipe the cleaner off the window then run the the window up and down a few times, clean any remaining window cleaner off the glass and repeat if necessary until the window rolls up dry.
Make sure both the window and the seals are completely dry before applying the wax.
Might wait a day or two before applying the wax.