Viper or Challenger
I think several people are overlooking something the OP said. New challenger or used viper so it'd be the same money. So there's no cost savings by buying the challenger. Actually you lose since you're taking the new car off the lot. Yeah viper mods are more $, but you'd be starting with a much better base car to mod from the get go. Plus figure in losing that warranty that comes with the challenger after you start doing serious mods.