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I had a 99' wrangler before the Camaro. They are really fun vehicles, It would be the car i go back to if I ever didn't have the Camaro. He's gonna have to give up the some luxuries because older models didn't always come with A/c, just heating.
I had the Wrangler for about a year and a half and never had any problems with it so it was quite reliable.
As for handling, Wranglers are notorious to flipping, but so long as he takes the corners as they were meant to be driven, then it'll be just fine.
Like I said, I LOVED my wrangler, but it is an aquired taste.
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