David,
I wouldn't worry about the 5:30 flight. By the time you get your rental and head out it'll be after 6pm. Just bring a few CD's, listen to some music, and you'll be at your hotel before 8pm. You can just daydream about the fun you are going to be having that week. I think you will be happier going up and over the Santa Cruz mountains in the daylight.
Ed, you remain the most optomistic person about drive times I have ever met. If Tony can get off a plane at 5:30pm at SJC and be at his Monterey hotel at 8, then every drink for him that weekend is on me. Note I assume he won't charter a helicopter to get down there.
My friend, the traffic on south 101 - or 17 - at that time of day is among the worst on this planet. He won't go more than 25mph until he gets to Gilroy (101) or over the hill on to 1 (via 17).
My advice would be to go have dinner somewhere in San Jose, let the traffic die, then follow Ed's leisurely drive plan. You'll get to Monterey and about the same time, with zero stress.
Rob - re Harding, well... I don't HATE it, I just do think they could have done so much more in the re-do, and what's there is just not worth detouring for... Sure you're plan of starting in SFO, playing that, then the leisurely drive down is decent - but man before you advocated trekking UP from Monterey specifically to play Harding! The first plan would be decent - the second madness.