Which compressor are you planning to use? All the ones Ive had have used a bleed valve between the compressor and the whip line. I'm pretty sure I have an in line bleed valve somewhere too.
The option to replace the front end of the tube with the upgraded cap and fill probe definitely sounds like the best outcome here though, I've just done this exact mod with my AA S200. It will be miles better than having the constant wear on the threads removing the cylinder every time you need to top up
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