I believe the matches that are included in the main part of the DVD will be clipped, similar to how WWE does the "From The Vault" segment on Confidential. The matches in the extras will be shown in their entirety. I could be wrong, but that's what I've heard.
I believe the Michaels vs. Jannetty match was an IC title match from 1993. Everyone else feel free to correct me, but I believe this was the blowoff of their feud with the cage introduced because Diesel (who had just debuted) had cost Jannetty the title previously.
First the post SS/road to WM thing.. Last year's road to WM started at the Survivor Series too when Brock lost the title and the whole Lesnar vs Heyman feud started. You could say Jericho vs HHH @ WM18 started at Survivor Series too.