The Vegas/LA/SF agenda is pretty ambitious, considering the amt of driving between the 3 places.
1/2 day - 1 day in Vegas is really all you need
Vegas > L.A. = 4-6 hours depending on traffic. Are you aiming for anywhere specific in LA?
L.A. > SF = 6-12 hours depending on traffic and the route you choose
5 will get you to SF the fastest (6-8 hrs) but your roadside attractions will be In&Out Burger, farmland, and cowschwitz.
101 takes a bit longer, but better scenery and more places for stopping on the way.
101 > 1 takes a LOT longer, but you get spectacular ocean views. It's not the best route for those who get motion sick from windy roads or those who are afraid of heights. I'd break it into 2 days if you opt for 101 > 1
101 > 1 Route
Central Coast Stops:
San Luis Obisbo > Madonna Inn for coffee/dessert (if you're feeling spendy, stay in one of the themed rooms for the night. (this is your weird roadside attraction)
Morro Bay > stop in this town for a little while, and take a walk along the ocean to the rock. Love it.
San Simeon State Park > Pull over and check out the Elephant Seals (I think it's better during the winter when the mammoth male seals are fighting it out on the beach).
Monterey/Cannery Row. Touristy, but I enjoy some touristy. AWESOME (but pricy) aquarium.
I agree the route is ambitious. My friend mapped it, we agreed that if anything gets cut for time it'll be LA. She's moving to the Bay area and I'm flying back from San Francisco, so that's definitely our end point. If we do stop in LA, it'll probably only be for a night. Not sure where our friends live but we both know a bunch of folks so we're not worried.
I actually hitchiked up route 1 as a teenager. It was totally beautiful (even w the creeps), and I recommended we go that way. Went to San Louis Obisbo last time, it was ok... don't remember much other than a 24 hour donut shop near the greyhound station we slept outside of.
Morro Bay looks awesome, I will definitely recommend we check that out. Monterey, too. Thanks!!