I am new to ss/fixed but have been cycling seriously since I was like 11 (28 years). You have a decision, on one hand save $$$ and upgrade your old frame, but as you say might as well paint it too, so probably like $300-350? Or get a new frame and put the old stuff on it. And once you get the frame you'll be like wow my new frame is so cool you may feel weird about putting thrifty components on it. And then who wouldn't like a new bike. I too am at the crossroads. I have an older Raleigh Competition road bike that I love (Reynolds 531), it is all old school stuff, non-indexed derail., etc. I have been thinking about having it painted or upgrading to a new road bike. The wife doesn't think I need another bike, so I was thinking about selling the Raleigh, but I love that bike it was the first bike I built up. Anyway, hard decisions to make. If money isn't too much on an issue get the new bike, I have seen you post quite a bit on this site, it seems like you are into it, treat yourself. Have you ever had a new bike? If you ride alot surely you'll get your moneys worth out of it.
Hey man this is the site of encouragement and postive bike energy, do it---do it.

Good luck with the decision. Keep us posted.

Greg