In my experience the main difficulty in replacing a fitting while leaving t he olive (and original nut) on the pipe is that the bit of pipe that projec ts beyond the olive might not fully fit in the new fitting. Typically the original pipe will have been pushed in as far as it will go before the nut was tightened. If the new fitting has a shorter 'bored out' section then y ou end up with with the olive, already compressed onto the pipe, being unab le to press against the fitting.
Robert