"I love that area though and a light rain would make it more fun IMHO."
Personally I agree – with the right rain gear. The redwoods can be a wonderland during a downpour – especially if there is some fog. I'm thinking of a particular location which is now in Castle Rock (added about a decade ago) down in the San Lorenzo gorge – below the ridge you hike on the Skyline-to-Sea route. I was hiking there during a big winter storm, and there were all these intermittent stream-lets pouring through the forest, there was fog and steam rising from the rivulets and it was like something out of a fantasy novel.
Drifting way off topic but since the OP is involved guess I may have permission…LOL.
I cobbled together an "unofficial" very nice "Silicon-Valley-to-Sea" Route a few years back. Takes 4 days (+ late day start first night), very varied – plus there is more of a dramatic feeling of accomplishment crossing the whole mountain range to the sea. I have done all parts (and alternates) of the regular Skyline to sea route so many times as day hikes (I live in the SC mountains) that there has been no particular motivation to do the whole thing at once. Plus this route takes you a couple of places you can't easily go on day hikes – hard to say that about many places in the SC mountains.
Starts in Los Altos, first night after a few hours hike from Los Altos on Black Mountain, second in Portola trail camp, third in Big basin trail camp, next day to the sea. More varied than the Skyline to sea. A little more of an adventure. You will not see many people on this route – or any over parts of it.
If anyone in the area is interested would be happy to share more details.