Well, obviously, I've chosen the former, but in the process of researching how to paint a bike, I've come across a lot of old bike people arguing that one should NEVER re-paint an old bicycle, so I thought I would offer my thoughts on the subject. The people who argue against painting (or at least painting it yourself) seem to be the collectors and aficionados--the ones who horde bikes in the garage and periodically set them all up in the driveway to look at them. They also seem to be the ones who derive much of their self-worth from flaunting their superior knowledge on various online discussion boards.
Their argument is this: there is only one "original" coat of paint, and if you strip it off or cover it up, you devalue the bike. I can see the point for rare and unique models, or especially antique bikes, but for the mass-produced late-model older bikes, I don't really get it. It's like an old house; you don't keep the original paint on the house, right? You repaint it, and sometimes frequently. Doing so protects the house and makes it looks better. And why hire a painter when paint and brushes are readily available? You save money and get the satisfaction of doing the job yourself.
My wife is a rare book librarian and I'm a historian, so believe me, I appreciate the value of a pristine historical artifact, but many old bikes are not historical artifacts. They are working machines that should be used and enjoyed. If a new coat of paint (done right and done yourself) is what it takes to enjoy your old bike that much more, then I say go for it!
And speaking of paint, I think I'm going to put on the last coat of red today. I'll update when and if I get it done.