We live on an island, or on a sailboat sometimes for 6 or 7 months, or in an RV camping and hiking everyday, or traveling around in small airplanes. All would be simplified by not having a dog. But we have a dog...
The 2 vehicle plan is a question mark. Part of it is the dog. We won't be staying in shelters, or likely Hostels or Hotels in town with him. Hitch hiking with him would be difficult. And like many have pointed out, bringing him brings the whole possibility of our success into question, which means not knowing where we'll be if we stop early. So we'll have our own transportation and hotel room/shower on wheels available. We'll also be able to take side trips to visit friends and family.
And we're looking forward to it!
Pete