I'm obviously easy to fascinate I guess.....I jammed with a colleague via the use of Skype last night. I live on Lake Livingston (Texas) and he's in Hobbs, N.M. Skype is essentially real-time with my connection to him (the little tiny bit of lag was totally unnoticeable and did not degrade our jamming fun at all). I connected the headphone jack on my computer into my amp and he did the same at his end plus we each also had our guitar plugged into our individual amps. We zoomed out just a little where we could easily see one another along with the fretboards as well. We plan to do this each Tuesday evening just to exchange ideas and try some new things together (and it's almost just as if we're in the same room together).

Skype will also allow the sharing of screens, so he can easily see my BIAB as the sound is playing through his amp at his end. With good computer speakers, you won't need to connect the headphone jack into an amp.

Just for grins, I thought I'd share this; the potential to jam is there with Skype......and it could easily be multiple people at either end.
cchallum