Damage claims arising from defects of or unrepaired damage to the road surface are sometimes accepted, and decided on a case-by-case basis, by the department that has jurisdiction. That would probably be Caltrans or the appropriate city attorney's office.
I get the impression here that
(a) it's a hypothetical case, which probably wouldn't interest them too much; and
(b) you'd have to prove that it was either a defect of or damage to the road, rather than just a characteristic of it that you should've watched out for; or in the latter case, that good practice for such a characteristic would involve a warning sign, such as BUMP or ROUGH ROAD.
Some jurisdictions won't pay claims until x days after a pothole or other damage has been formally reported. (Generally speaking they DO want citizens to report genuine problems in an accurate and timely fashion -- we drivers collectively see a lot more than the department ever could!) See for instance or (your favorite search engine can come up with examples specific to your area).
There are a lot of gray areas here (and the gradation of the gray scale might vary a lot from one jurisdiction to another -- claiming "governmental immunity" is a pretty common response in some places). There's a balance, somewhere in there, between the highway or street department's duty to keep things in reasonable shape and the driver's duty to know his or her car, keep an eye out, and behave accordingly.
And when you are talking about basic characteristics of a road rather than a pothole or suchlike they might say it is not reasonable to expect that all roads will be equally well suited to any arbitrarily selected car... or that they can respond immediately and effectively to some road problems that call for major reconstruction.
Unfortunately for the trip you describe, there are some Sisyphys-tackles-the-Augean-stables stretches of road where the combination of geology, traffic, and lack of money might well mean that if certain stretches ever *are* really set right they won't stay that way...
--Joe
