Having a new bike now, after having a pretty beat up old one, with bikes, I'd definitely go new, especially since AVL Classics aren't going to be found much in used. With cars it is different, and I would always go for a good used one, but with bikes, too much may not be right, and better to start with a clean slate. I'm that way with outboard motors, too - you just don't normally know what one has been through - although there are exceptions.
Then, once I had a nice, new bike, I would look after it well - never being satisfied with half-assed work on it, whether mine or someone else's.
My tendency is to think too much about initial cost, and not always get exactly what I want - then, when I do get something satisfying, I quickly forget the extra cost.
An R E can be a new outlook on life, and well worth the money. I would look at it as a long-termed investment, and keep it that way.