My answer... not always. Case and point, driving. It has been my experience that there is no correlation between the number of years of experience and the quality of the driver.
Every single time that I'm on the road, all I see are terrible drivers. One missed accident here, a near side-swipe there, failure to signal, limited driving distance, short stopping... the list is endless. It happens left and right.
Driving is one of the few acts where practice boosts confidence to take risk rather than make perfect drivers. Most other things people do, you can gain confidence and become better. For example, the more you play a sport, the better you become at playing it. The more frequently you practice an instrument, the cleaner and crisper your music sounds. The longer your tenure at your job, the more you learn, the more efficient you become, and the better is your end work product.
Drivers seem to get worse with more experience. Maybe that's why insurance companies can charge the premium for coverage. I feel like that almost justifies the high cost.
How can we combat the rise of the poor driver? To me, it's easy. Like most professionals in any career path, there is some sort of continuing education. Drivers should be required to take their drivers test every few years. Maybe every time their car goes for registration renewal, they have to get their driving skills re-evaluated. Who knows? It's something to try to make things better. And in the process, jobs could be created, money could be made, and safety could be insured. And maybe insurance premiums could be reduced!
Did I just find a solution to a 1st world problem?
Be careful out there...