I think when the owners occurred could have something to do with it to, as well as your plans for the car. You figure the market recently was crazy for Vipers, so I could very well have seen two to three sales over just the past few years as people could have been trying to buy and flip them. Also, the Viper really isn't a car for everyone. They are not luxury automobiles as most people think of them, so a lot of people find out pretty quickly that the car just isn't for them, so I could understand that leading to several owners. That happening on the same car is maybe a bit odd though. And as far as auctions, I'm not sure I'd be as worried about that, but without knowing more about who had the car first it's hard to say. If someone traded it in on a different car at a non-Dodge dealership, I think most of the time they end up going to auction. A Chevy or Ford dealership might not want a Viper sitting on their showroom floor next to their sportscars.
The other thing to consider is why you are buying it yourself. If you don't plan to keep it long term and intend to sell it down the road, then I would agree it probably makes sense to buy something that might raise less eyebrows. If you plan to hang on to it for a long time I wouldn't really worry about it, provided the car is in good shape to begin with. I always say I don't buy my cars for the next guy, I buy them for myself. I'm also not really afraid to tackle any job I might need to to fix something that could be broken (aside from body work, I don't have the patience for that, lol). I've rebuilt my engine twice now after spun rod bearings and pulled the entire dash structure out of my car to diagnose a broken temp door on my HVAC box, but I also have zero intention of ever selling my car.