This year will be worse attempting to get to TTC/MK without being on the pre-0500 buses. The better bet is to try for either the AK front gate or WWoS. As a 10-11mm runner, I do not think both are really possible unless all cards align. I am not 100% sure that grabbing the first AK bus from CBR will work as you will be past the gate about 30-40 minutes before rope drop, putting chances of getting there by bus a little iffy. I know he could drive and get there in fine fashion and watch you pass. What is not clear in my mind is how one drives back out of the park since we are using the primary auto parking lot exit. There may be a way out through the Toll booth service road and then backwards up the lane
but I do not believe that is used regularly.
That leaves the WWoS. If I were him, I would give myself 90 minutes from CBR to ride either a Marathon or regular bus to Epcot then take the Marathon WWoS bus
OR just drive to WWoS. There will be a slight back up at Osceola where he will be directed to the right lane of the outbound side of Victory, but will be able to park and watch you from Champions Field.
No, the Main Street of MK will open at 0530 for spectators to watch free of charge. They do sell coffee and a few items to eat while you wait. All other parks will require a ticket. Though, the only park I would actually enter to watch from would be Epcot near the IGate. All other parks I would watch from outside the front gate.