Some things to consider ...
Trail conditions dictate how long the train is. For example, if parts of the trail are fine sand and there is little cross wind, to keep yourself out of the dust cloud of the truck in front of you (a very good idea) we all need to drive very slowly (boring) or we all need to hang back a quarter mile or more from the next truck.
Under those conditions, a 12 truck train is now 3 miles long. We want (need, really) radio communications between the lead and rear vehicles. Will we have it? Dunno. Depends on conditions.
If we encounter an obstacle that requires spotting, more is not merrier.
There will likely be scenic spots along the way where we'll want to stop. Is there adequate room for parking or if it's a dead-end or hill climb, enough room for all trucks to park and enough room for U-turns?
In a long train the lead vehicles get to see critters. "Hey, a pack of wild hyenas at 11 o'clock!" is good news for the front. It's a bummer in the back because the critters will surely be gone.
I'm not being negative, just practical. An army of Hummers is fun to think about but not necessarily fun on the trail.
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