Having done the Large Pickup, Larger load in my youth, I would rather you didn't try it. Prob be more tickets than travel.
However, I have had thoughts of modifying a light semi lowboy trailer, purchasing a good older light semi tractor and having a "Baja un-bash" travel setup for 'shoreside crusing'. Back from Baja any time of the year? Down for a month? Maine in the spring? Joint owned?
Any intrest ou there?