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A couple of things to consider. First, for all but the lightest trailers, get a frame-mounted hitch. You will likely need to have one custom made, since the bolt-on ones for these cars are long out of production. Second, get a trans cooler, the bigger, the better. Third, the real limitation will be the brakes. If this is a four wheel drum car, proceed at your own risk. If it's a disk brake car, consider upgrading to the 11" rear drums from a 73-77 A-body (yes, I am aware that the VC already has bigger 9 x 2.5" brakes). Finally, get a set of AirLift bags for the rear springs (as opposed to air shocks).
Properly set up, you should be able to tow 5000 lbs with no problems.
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Joe Padavano
64 Jetstar 88 Conv
66 442 L-69 Conv
68 W-30
69 H/O
69 442
70 W-30
72 442
84 Custom Cruiser
86 Caprice wagon (w/307 Olds)
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