Logistically towing two cars on two trailers would be a PITA as well.
Load Datsun, strap it down, secure ramps. Walk second trailer into place and hook up. Load F500, strap it down and secure ramps.
Drive to venue making sure you NEVER have to reverse because you just can't.
Unload F500. Disconnect trailer and hand walk it out of the way.
Unload Datsun.
I feel like the single (longer) trailer would be about 500% easier and safer.
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