Two people are actually able to play at the same time, I've done this myself before and as far as I can tell steam has done nothing to block this.
If anyone can prove it's not legal/within their terms then please comment below.
If you both share a game on steam, then both of you download the game.
If one of you goes into offline mode, you can play at the same time.
This obviously blocks online features such as saving to the cloud and online gameplay but considering skyrim is single player ( without mods
) it shouldn't be a problem.
This will also not work with games that are DRM which require you to be online to start play.
gaming.stackexchange.com/users/143457/S.Wessels
Two people can't play at the same moment on Steam Family Sharing.
Family Sharing FAQ clearly states this: Can two users share a library and both play at the same time?
No, a shared library may only be accessed by one user at a time.
gaming.stackexchange.com/users/87186/Ave
This is completely possible depending on the game (usually games that do not connect to the internet).
After setting up family sharing, the person who owns the game must start the game.
After the game is running, go to steam and go into offline mode.
Now the second person can use family sharing.
I've done this numerous times with Civ V
and i believe should work with Skyrim.
gaming.stackexchange.com/users/148316/Christopher Powroznik
From the steam website FAQ: Q:
Can two users share a library and both play at the same time?
A:
No, a shared library may only be accessed by one user at a time.
gaming.stackexchange.com/users/64871/Vahx
You can't.
Family sharing acts as though you were passing the account login back and forth.
Only one person can access any given account at one time.
So as soon your brother starts a game, you or anyone else is locked out.
It will not let you play as though you had two copies of the game.
gaming.stackexchange.com/users/95753/Radhil
My brother owns Skyrim on steam. We use Steam Family Share, but we were wondering how both of us could play it at the same time?
How to make two people play at the same time?
gaming.stackexchange.com
<steam><steam-family-sharing>
gaming.stackexchange.com/questions/251372
gaming.stackexchange.com/users/135613/Ivan Hammar
 If one of you goes into offline mode, you can play at the same time. Two people can't play at the same moment on Steam Family Sharing.   In order for two players to play the same game, via steam library sharing, one user has to play in offline mode.
Players suggesting that it is possible. While few others are stating that is in't possible.