The way you describe the financials, there does not seem to be a benefit to buying new. I'd keep in mind, however, that you would have better luck having the price reduced with an individual than the dealer. If I understand correctly, the smaller, cheaper bikes don't have much of a margin for the dealers, therefore less room for haggle. Also, dealers are very skillful at adding fees and extras to the new vehicles. I watched my friend complete the transaction for a brand new Vulcan 800, and I was horrified to hear of the VIP Card for which he dropped an extra $1K.
Another downfall to owning a brand new vehicle is the expectation of perfection. Any little thing that sounds odd while riding will keep bugging you: "Is something wrong with the bike? Do I need to go to the dealer and check it out? This thing is BRAND NEW, it shouldn't be doing that!" This one will depend on the individual, but I do know a guy who sold his Honda VLX less than a year into a brand new purchase because "he kept having problems with the Honda", meaning both the bike and the dealership. I don't know ALL of his details, but I recon that he had a hard time affording it to begin with, and not having a PERFECT experience was too much for him to handle.