When to respray bike?

If the paint is intact enough that corrosion can get a hold then refinish it. Authenticity is all.well and good.but is meaningless on a frame damaged by corrosion.

From the photos a it looks tatty but intact. I'd be inclined to clean it up and leave it for now.
 
Firstly you should know I do bicycle re sprays, restorations, and custom paint. If you came to me and asked the same question and stated the same usage information... I would suggest elbow grease and the vinyl graphics. Please take into account I would be losing a spray job in doing this. It's what is best suited to your situation, barring any unseen rust or chips not visible in the pictures. They can always be touched up in most cases.
 
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