I collect vintage everything; Cars, motorcycles, clothing, music stuff, etc... It's just kinda my thing, you know?
I mean, riding a modern bike would be more convenient and perhaps a bit more reliable but, I can't really see myself riding one. Money's not the issue, it's personal preference. Especially when it comes down to styling. I love the retro 70s colors and designs. As far as mechanical, I mean, it goes both ways: Older bike, you're more likely to be on the side of the road but usually have the ability to diagnose and fix it on the spot (granted you've got the tools); newer bike, you're much less likely to be on the side of the road but, if you are, you're most likely screwed. Especially with the fuel-injection systems and modern electrical.. Nope, it's vintage carburetors for me!
Oh yeah, 90% of everything I buy is off Craigslist haha. Second-hand for life!