IMO if I were in your shoes I would definitely not buy new. I might not even buy a Big Dog. Dont get me wrong I love these bikes but they will take a lot of care and you need to be able to turn a wrench or have lots of money for a mechanic (maybe you can I dont know). If you buy a used Big Dog and dont know bikes that well I would hire someone professional to look at it for you.
I bought my first BD from a small dealer and had it shipped to me. There is a lot that pictures dont show and even video. I would never do it again because there was far more wrong with it than I realized and had I seen it in person and rode it I would have never bought it. I had to put a lot of work into it and money. I am selling it and I am going to lose my ass but it was a great learning experience for me because I love to wrench on cars and trucks of my own and got to talk with a lot of great people here on the forum who helped out.
I would go to any dealers around your area and check out all the types of motorcycles I could. Then go to a place like rumble on and save a lot of money on an almost new bike with out all the dealer shit. They have lots of Harley's if you like them. Just my

Sorry for the rant but I have learned a lot in the last year. I am a returning rider and hell I might decide one day that's it I'm done or I may ride until I fall off. Why because I can
Don't stress to much about it just take your time and check out all the bikes you can in Person. I cant stress that enough.