With every bike I think about custom paint. But all I've done is think about it! It's a lot of money typically but makes your bike totally unique. I think no matter what your bike will be out of style at some point. What we call old school now was totally obsolete 10 years ago and not in style. If you're gonna keep your bike then the money may be well spent. If you plan on selling/trading it you'll never get your investment out of it. I think looking at the possibilities is most the fun anyway. Of course this is my female perspective on it! I always tell my husband I could buy a new sofa or paint my bike. He always votes for the bike!!
I just got a custom paint job last week on my Street Bob, I just wanted it to look different from the other Streetbobs running around. I've had lots of bikes and I've never had one custom painted before. I really love the paint job, but now I'm so damn worried that I'm going to scratch it or it will get keyed downtown one night that I don't think I would do it again. I could have vacationed for a week in the Bahama's with the money I spent on paint job and if I had a do over thats what I would spend my money on. Just my opinion.