Wondering

Wondering...If there might be a correlation between a history of obsessive masturbation and length of time to achieve ‘rewiring’.

Perhaps, but I don't know of any surveys investigating such correlation. Long established personal behavior habits are stronger and more difficult to change than newer developing habits. The rate of success changing any particular behavior is largely dependent upon the aggressiveness of effort and positive attitude toward effecting the change. Your ego may be directing the conscious effort to effect change but unless your Id is also in support all your efforts may be for naught. Only some honest self analysis can reveal the depth of cooperation of your Id.

The path toward generating prostate based orgasms requires a paradigm shift in thinking from both your ego and your Id about what constitutes an orgasm and the methods needed to achieve these new orgasmic experiences. IMHO, the quickest path to achieving prostate based orgasmic success is temporarily dropping prior peniscentric masturbatory behaviors (please see the post Penis, NOT) and practicing some form of temporal abstinence (please see the post Aneros, Arousal & Abstinence/Semen Retention). These two behavioral changes can leverage your already powerful life force energy into accelerating the learning process/journey of the Aneros experience.
Good Vibes to You !

Personally I masturbated 1-3 times a day my whole life (since I can remember) and my re-wiring didn’t seem to be hindered by it.

Have masturbated frequently since my youth and have experienced rewiring after a little over a year!