I've been to the top 5 or 6 times (hiking from the bottom) and I do shorter training hikes on the dirt road as often as once a week. The trails make for a much nicer hike, though the road is convenient.
This was my first time reaching the top - I hiked the road to the top on a day when there were high wind warnings in the area. Gusts were about 60 mph on top at times, but the views were amazing!