If Barb's Minivan wasn't a Chrysler product from the early 2000s, it's plausible to think that it could work; just change out the Minivan for an Early-Mid 2000s GMT360 platform SUV (Chevrolet Trailblazer, GMC Envoy, Oldsmobile Bravada, Buick Rainier, etc.), and it might just work.
Though, the real issue here is Chris may not be able to adjust if, at all, he's never exactly taken many trips outside of the General Charlottesville-Ruckersville Area, unless it was for the sake of his "Love Quest" or Conventions (even contemplating taking the ol' rustbucket caravan up to Washington for a Brony convention, despite its shortcomings.), and really the only people he talked to IRL right before Jailtime was his imaginary love interests and Barb.
But, despite all that; I Somewhat agree with you on that front, Chris discovers more of America, Meets new people on his travels, and may actually gain some form of normalcy and potential sanity back that he had lost in the last decade.
After all, it might be Chris's only option as I have a feeling Barb's either gonna be dead or in a nursing home, or Chris is gonna be barred from re-entering 14BC by the time he gets out of the slammer.