For that long of a trip, why can't you do both Aspen & SD? Head to CO, then over to CA through Donner's Pass, then the PCH south (take a little bit of a detour north through the trees), then back east. Stop off at Cero Gourdo, Vegas, etc. Find a place halfway to do an oil change (hit up members for to do a meet & greet and change oil in their garage).
Will be at least a 5000 mile trip but still pretty epic.
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