physics would dictate that the more refined your edge ultimately the more evenly spread along the edge the force is and therefore the edge should, in theory, sustain more abuse before dulling. There are a few problems with that- I find when I strop my knives I have a pretty damn hard time slicing ripe tomatos. I also suspect the longer your sharpening regimen the more likely you are to start putting funny bevels on the knife, etc. More or less, the longer you put the knife to the stones, the higher the probability that something could go wrong. Experience sharpening notwithstanding.
at the end of the day sometimes I think we go overboard and the "knowledge" that you just use a 1 micron or finer abrasive to hone your edge can sometimes be worth more than any utility that edge is going to provide (or lack thereof)-- what's the point of having a super sharp knife if you once again need to saw through ripe tomato with it?
Then again.. I strop my tojiro DP nakiri every time I sharpen it... doping with chromium oxide and it absolutely falls through stuff like celery, leek, carrot.