tdaver, this whole thing sounds ridiculous but I think you know that. Flying sucks right now. Long necessary driving sucks right now. Everything's inconvenient. In my experience, you get better service from a dealer you bought the car from than you would your local subaru dealer you spurned, if you'd be getting service from a dealer. I'd guess there could be some extra hoops to jump through with registration after buying out of state.
But if you're compelled to save $2K less expenses of the trip, don't pick the nearest places or even a destination place you're intrigued by. Pick based off what you want your first leisure road trip to be that will double as you having to drive home.
And you should probably transport something to further tip the scales in your favor, either as a good deed or for profit. Maybe adopt or facilitate the adoption of a dog from a place that's overburdened and bring the dog back to your town. Or take advantage of the post office being decimated and try to get people along the route to pay you to deliver things.