No one can say with any degree of certainty, what the historical Buddha thought about this matter, as any words of his are filtered through millennia of interpretations.  I have often felt that were his "enlightenment" possible without the extreme austerities he practiced, he needn't have deserted his wife and child.  But that was his destiny and each soul follows their own path. 

I am, however, certain that he never regretted anything about his mortal existence.  His views on Samskara are well recorded by his disciples.  At least, regarding celibacy and worldly possessions.  Perhaps in this time period his life would be somewhat different?  Again, it's complete conjecture on our parts to ponder over his regrets or lack of regrets. 

While this notion is most intriguing, it really serves us little to conceptualize about another's experiences. What is primary is the example he left and his profound teachings.  It's all about stopping the mind and taking direct immersion within the Infinite Light of this present moment, perpetually awakening, right here and now, an eternity in the making.   :!: