1. It's a possibility, and has happened before, but there's no way to tell
2. A lot of people ask for this, but the problem is we need pretty much ALL the mods to be updated before going up, so this would effectively be the Technic team saying "Waiting for mod to update...", "Waiting for mod to update..." etc.
3. Updating the mods works fine, you just need to delete the previous version and make sure you're using the Bukkit port.