But frankly, I think you're exaggerating the shame due to you for riding a Bonnie. I mean certainly riding a motorcycle that was designed specifically to be a throwback - ignoring most advances in modern safety, aerodynamics and ergonomics - will peg you as someone who values form at least some modicum over function.
I think that somewhat mis-reads the retro market. It's not comprised of people shopping for modern bikes who want something with more style, but people on or looking at old bikes that want something new. Not new in terms of the latest technology, but new in terms of no concerns about age-related issues like rust and metal fatigue. You don't get a new Bonneville over an R1, you get it instead of an old Bonnie, so the advances aren't on the table either way.