In theory I do agree that's a good idea, and it honestly does have potential to work.

But then there's also part of me that's afraid it will have the reverse effect.
Mainly because what I've noticed in both OT and Spam is people will pick those who they like the best and then began interacting with them off-site a ton (Steam, Skype etc.).
Which is great at first, people communicate more, know each other better etc. But it seems to have a side effect that eventually they find that they're are perfectly fine talking through said program, and don't even need the Guild anymore. 

That or they decide that they dislike either a few members, or a general community on the Guild opposed to said friends. So they in a sense migrate off simply to not deal with the 'unwanted' people.

Now, obviously we can't do anything such as say "Not allowed to talk with Guild friends off site", nor should we do that.
Like I said earlier, it is infact a sound idea and it could work. But we would want to make sure it's not done in a way to encourage small groups/cliches to pop up and eventually cause separation/division as a result.

Plus, generally for such chats to work we need a generally active site/community to begin with. 
I mean, if the site itself has a lacking community who is going to think the skype group is any better?
I will note though we do have an IRC currently, that does kind of function for the purpose you describe.
But those generally have the issue of still being Guild Moderated, even if not the forums directly so it has far less of the "Let's get to know each other off site" feeling.

+Speaking personally, last time I was in IRC one of their Mods (They were in and out too quick to even grab a name) banned me over a small joke simply because (Their words) 'They were too busy with Gay Porn to be interrupted by IRC stuff'. 

Now, personal thoughts on that aside (I'd rather not turn this thread into a "X Mod is a prick!" sort of thread) it does still address the issue of it's not exactly an off-site conversation place if there are people sitting around who could ban you, may it be for personal reasons, or Guild regulation reasons. So yea, we do somewhat have your idea already. But it could be better.

So basically:

-Need an active site first, to encourage people to use off site chats
-Said off site chats need to help encourage community and involvement, not cliches and divisions
-They would need to be unconnected to Guild Moderation, or it defeats the purpose by simply becoming a Guild extension.

In the original topic I had already proposed trying to get the Admins to get around to making the contest topic that was promised.
We had several groups of people (One of which mind you, I think is gone. Seeing the complete lack of activity it's members have shown this past month) who were planning/working on said contests to help boost activity.
But needed their own section for it, because simply squeezing it into others has normally caused it to be unnoticed, cause people don't think to look for it, and therefore it misses the eyes of most the community.