You've actually picked a pretty good floorplan from a very reputable manufacturer. The new/used discussion is something to consider but be aware that the Winnie will hold value a lot better than many other brands. I'm an advocate of trying to find a well taken care of used unit but wouldn't have a problem buying the Winnie new.
You look to be in good shape weight wise as long as you don't get stupid with loading the rig. Check the cargo capacity of your truck but I suspect it's in the 1200-1600 pound range and should be just fine with 500-600 pounds of tongue weight.
I'd be careful about getting one in one of the wild colors they offer. It might suit your style and personality but could cause a problem a few years down the road when you're looking to sell it. Bright colors might not be in fashion then. I also might rethink the instant hot water. They're relatively new technology in RVs and the old reliable gas/electric 6 gallons water heaters have been around forever. Parts might be an issue. I guess I just don't know enough about them so I'd stick with the tried and tested.
The price you mentioned is a little on the high side but I've found that most dealers don't discount a lot on the Winnebagos. Good luck and have fun. And never, never trust an RV sales person. Some will steer you wrong just to sell the unit, some just don't know anything about towing or using an RV. Not saying they're all bad but there's no way to tell one from the other. Kind of like an internet forum, about half the info you get is trash. You have to figure out which half. :h
