Depends on what you want out of it. If you hope to sell it someday as a classic, vintage bike, then you won't be doing yourself a favor by painting it. If, on the other hand, you like the bike, and just enjoy riding it, and you have a vision of a new color scheme that would bring you some happiness, and you can afford it, then IMO you should go for it. I have an old bike myself that wasn't ever going to be a true C&V worth $$, but it had sentimental value for me, so turning it into a fixed gear bike became a project for me that I really enjoyed and learned a lot through. Oh, and more to the point, I had it powder coated, and think it looks great!