Unless you really do an engineered job, you will continue to have to do maintenance.
The first thing that is required for a fixed job is keeping the water off the road with a change of cross slope and install collecting culverts. The hill side of the road then will be lower that the outboard where a ditch is dug at the hill side. The spaced culverts will take away heavy flows before the ditch gets so loaded that that is eroded. Ditch probably needs paving with rip-rap placed on geotech fabric.
Farther up hill, diversion ditches will help reduce the flows that you have to handle.
So a real fix takes a lot of work and expense.
Chip seal or blacktop paving will not solve things, unless water flow over the surface is controlled, especially at the edges. Fixing washed out paving is more of a job than as now present.