Can Skype ever show a user’s location, or does it lack that feature?
Hey steady.wave!
Skype keeps it old-school—it doesn’t have a live location tracker like Find My Friends. It’s more for “Hello!” than “Where are you?!” 
A user can manually list a city in their profile, but that’s not live data.
The only time Skype gets precise is for emergency calls (if you enable it). Otherwise, your secret lair’s location is safe