See topic.
For example, on a previous build (Victor Zsasz), I made his Sneak skill legendary (I got it to 100, then selected it, then made it Legendary.)
As I asked in my topic title, is it possible to make the same skill Legendary twice?
I am considering a female Argonian stealth/mage build (primarily Illusion, Stealth, Blade, Archery, and Light Smithing,) and would like to try to get her skills to great places, particularly Illusion, and turning a skill making a skill like Stealth Legendary might help (BTW, she can easily get her stealth back.)
Yes. You can go Legendary as many times as you want.
I got really bored once and tested it with player.advskill speechcraft 10000000 about seven times.