Yeah man, for awhile I was bummed about my bike being 'old' and a 'classic'... then I was able to take a ride on some other bikes: an F4i, 2002 R1, etc. Upon doing that, I realized that I really ENJOYED my bike, the way it felt, and the way it rode. Now, I'm still a poor college student riding an old bike, and I still get questions from people about when I'm "trading it in" or "moving up". By this point, between the resale value of my bike, and the investment I've made into it for maintenance and upgrades, I could've afforded at least a sizable downpayment on a repli-racer, or the purchase of an SV650s.
I have no interest in selling this bike, I plan to purchase more as funds become available, and I plan on owning them in addition to this one. That's pretty damn hard to explain to people when they ask when you're getting a 'new' bike. The reality I've come to discover is that people who are concerned with what bike you own or ride, are typically the people with their heads buried so far up their asses that they can't distinguish motorcycling from it's new, pop-culture representation. Never be down on your bike if you enjoy riding it; riding it is what the sport is about.