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Old western flyer. How old though?

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Would it be sacrilege to even consider painting it?

i'd say without hesitation: leave the paint orig.
although it's not a particularly desirable or valuable bicycle, there's no shortage of bikes with worse or non-existent original paint out there to re-do.
it'd be far easier and cheaper to enjoy the bike. as it is after a sympathetic mechanical service, and it'll get more attention if left original.
 
So much knowledge here. I learn something new every day.
I had no idea any bike in the 50's would still have a skiptooth set up?
Still using prewar left overs at that time?
 
I have given it a little go over with some WD40, aside from making my house stink, the bike has started to come up amazingly nicely. So much dirt on it! I thought it was just lots of rust!

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