Hello - My wife and I are retired US expats living in Yucatan, Mexico. The import permit on our van is expiring so we need to take it out of the country. In September we are planning a long road trip back to the US ending up in Chicago where we will sell our van and then fly back to Mexico. A little bit about ourselves - we are in our mid 50's, we like museums, some light hiking, sightseeing, and urban exploring. We plan on staying in Airbnb and mid range hotel/motels along the way

Our rough itinerary is this:
Day 1 - Merida to Villahermosa
Day 2 - Villahermosa to Puebla
Day 3 - Puebla to San Miguel de Allende
Day 4 - San Miguel de Allende
Day 5 - San Miguel de Allende to Monterrey
Day 6 - Monterrey to Fredericksburg, TX - cross border at Colombia
Day 7 - Explore Fredericksburg, visit LBJ ranch and then drive to Austin
Day 8 - Austin
Day 9 - Austin to Oklahoma City via US 281 and US 81
Day 10 - Oklahoma City
Day 11 - Oklahoma City to Joplin,MO via old Route 66 then detour south to Bentonville, AR
Day 12 - Bentonville - Visit Crystal Bridges Museum
Day 13 - Bentonville back north to Joplin and follow Route 66 to St Louis
Day 14 - St Louis
Day 15 - St Louis to Springfield, IL - visit Lincoln museum and monument
Day 16 - Springfield to Chicago

Does this seem doable?
We can probably fit in an extra day or two if there is anywhere else along the way or in the vicinity to visit or spend time

Thanks in advance for any info