I also have. 91 V2500. I wheeled it for 2 years no lift and 33's. but I dragged my rear receiver hitch more than the rear tires were in the ground(At least it felt that way). I put a 6" lift and 37's. it is a little tall but the rear overhang it a killer. It is a great rig and I constantly surprise people with what it can do.
Here is a pic of the flex I got out of it with no lift and 33's.
And here is with the lift and tires.
I just picked up a used Ramsey RE12000. $200.
You will need a winch. Everyone I wheel with has jeeps. Little small to help out if I get stuck.
My stock with 33's did fins and things at Moab with no problem.
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