Not Ranked
I have a 18' Cargo Mate Qualifier. 3' side door. 8'-6" wide but upgraded to 5000 lb. axles. Originally bought to pull my SPF around, but recently purchased a '65 Mustang fastback vintage racer. It's doable, but tight. The Mustang has 1" lowering blocks, so the door scrapes on the top of the wheel well. The front overlaps the side door about half way, so it's tight accessing the front of the trailer.
I prefer pulling the 18', but if he can wait for a 20', it's probably a better decision. But, I don't agree with needing longer than 20.
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Steve S
F-250 w/ 6.4 Diesel
SPF #968 w/ Genesis Aluminum 427 S/O
CVAR vintage racer: 1965 Mustang Fastback w/ HP 302
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