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I drove from San Diego to Key West FL and really lived the drive. Then 11 years ago I drove from San Diego to Ohio. It was a very nice experience and while it is nice to have someone to travel with you could do it yourself. I took the "10" all the way across and then 95. I would not sell the car until you get to Boston and can size up the local transportation options.
Plan the trip out and try to see some sites along the way. Make sure you understand the weather patterns.
I really enjoy driving across America and plan on doing a 1 year trip once I retire.
Don't let people talk you into missing the adventure of a lifetime. I drove across the country alone twice and had a great time. Yes, I'm a guy, but nobody is going to attack you at a hotel or restaurant. I say go for it!