Hey Zeke, Kool thread!
I can at least relate a little to this, on my "Garage" pics, I show my 9C1 Caprice pulling my Sunbird on the open trailer pulling my second trailer. I used to do this on occasion from the Grand Bend area to the Kitchener area when going to a show and needing to transport extras along and dropping off the smaller wagon at my son in law as we built and shared the smaller trailer. I would always pull out and pass other traffic, especially on the 4 laner between New Hamburg and K.W. and sit and chuckle as my Ole Cop car an two trailers would go rumbling past to the shock and amazement of other drivers lol.
As my cop son in law would laugh, he told me that it was such a grey area that it wasn't worth the trouble to pull me over. The Caprice was built on a 1/2 ton chassis and the combined units were under 9000kg.s the Caprice has larger axles than the GM half tons and are one size built specific for that vehicle only and do not interchange with anything else..(found out when I towed the Sunbird to Alberta) pulling out and powering past other cars was a blast with one car on a trailer but with two trailers, just blows'em away, even more fun when standing on it and pulling away from the lights and leaving the 4 bangers behind, now that's torque!
"remember... not everything is good on TOAST!"
3 Birds of a Feather...
#1 the Silver '80 W-66 code Formula purchased 9 years ago
#2 red "80 W-66 code Formula purchased Mar./16
#3 black '78-9 coupe with spoiler kit and 4spd 305...parted out to a Terrific H-Buddy
2015 Cruze Turbo Diesel/ Just replaced by the 2016 Sonic
'98 GMC 1/2 ton with corporate 3/4 ton driveline still makin' it all possible