I suppose that the keys will lie with state law dealing with the nature of the city's duty, whether the condition of the hazard breached that duty, and whether the city has some form of immunity. And on the other side, the amount of duty to keep a lookout the cyclist has under these circumstances.
I'm convinced that bicycle paths designated by authorities should be designed, constructed, and maintained to be safe for reasonable conditions. This would include being safe at night for riders with basic lights (read "no holes, dips, root bumps, covers, plates, curbs, posts), being safe for a mix of traffic in the days (read "clear markings, clear sightlines), being safe at reasonable bicycle speeds (read "fast"), and being clearly integrated with other transport modalities so that intersections and parallel stretches don't cause trouble. This is possible, but would take thought, commitment, and money. Short supply of all.