1) You have history with the bike having bought it new. That to me expands the "zone" of what I'd do to keep it roadworthy.
2) Because I'm a stickler for symmetry I'd rebuild the front wheel. It's likely that Wolber rim might start to exhibit the same flaws (if it hasn't already). I think the Ambrosio rim looks awesome on it.
3) It is, even in the small pics we have to ogle, a beautiful bike in great condition.
4) I would forgo the repaint as well, clean, little polishing compound, wax, ride.
5) Replace the headset as finances allow...it's not that expensive.

You have a great ride there. If you are committed to riding I think you have a great bike there to do it on...just take care of the small issues and enjoy the heck out of it.