I'd only say this one is really customized (Dead influence or not) and since I always buy anything with an eye to resale, I'd be hesitant to buy anything this specialized (paint, the jockey shift, etc.). If it's really lighting your pilot, only you would know.
If you've got the itch and it won't cost a fortune to get your old ride on its feet, H-D is way off business-wise from just a few years ago when over-list prices and long waits were the norm. They've summarily closed Buell this week for good, looking for a buyer for the just-purchased MV Augusta, and likely looking to close their plant in York, PA. As most of their dealers built palace-sized dealerships in the last 10 years, you might find a very receptive climate to trade on a new one. And of course, there's lots of Stars, Victorys, etc., out there in this style of bike.
Good Luck!