Good to know about the dirt road. I have a Volvo station wagon as well. Either way, I would be doing White Mountain prior to the road being groomed.
I figure that most of the "old-timers" have no problem with solo summitting Whitney. I'm not a very experienced hiker, and don't have the high altitude experience. I'm not so much risk-adverse, but rather risk-mitigation oriented. If I cannot sufficiently mitigate my risk, I won't do it.
I have an appointment scheduled with my neurologist to discuss Diamox and altitude in general, I have regular apnea. (Apnea is one of the reasons I prefer a day hike.)