This sounds awesome! I love those Jack Taylor tandems.

I think for touring the Pacific Coast, it's generally recommended to go North to South to take advantage of the prevailing winds (unless it's santa ana time).

I'm moving back out to San Diego in May or June, so just to throw another option out there: you could ship the bike and assemble it there, pedal around san diego a bit, then hop the Pacific Surfliner amtrak train (allows you to roll bikes on) and ride that up to San Luis Obispo to get beyond the LA traffic congestion.