I do'nt think I've been on the 299, but every highway that I know of between Santa Rosa and the Oregon border that connects the 101 to the I-5 isn't a straight shot. The roads have ot go through the mountains and are thus very windy. Shouldn't be a big deal if you're not in a hurry, but if you are, I'd say get to the I-5 as soon as you can. BTW, the 101's not all that straight either, but you probably know that.
Also, on the car not starting, my guess would be that the engine's seized and unsalvgeable. You probably shouldn't get the car. Oh yeah, what's the seller's phone #?
Seriously, good luck! Sounds like a fun trip...if my girlfriend could handle the windy roads and the suspension on my 300D was perfect (still needs guide rod mounts), I'd love to take a drive down Hwy 1 to L.A.
