I'd put $100 that a tesla will be able to take you from start to destination without help in no more than six years, and I think I'm being conservative.
I was going to say the same thing. GP and I could design the bet with assumptions like "most of the US" and "good weather" but that's riddled with issues from a contractual standpoint.
So how about it has to take GP from his home to a destination 100+ miles away, the car has to park itself in a legal spot, and it must reverse at least once during the trip? And I'd like to see it done at least 3x, including once when it's not perfect weather (could be foggy, moderate rain, light snow - whatever).
With conditions as you've described I would still happily bet $100 that no later than 9:00am EST Oct 9 2026, a Tesla available to ordinary consumers will be able to perform the task with no driver intervention.