So a "Can Do" attitude is flying below VFR minima and an attitude that places you in the managers office two or three times?
Perhaps instead of slagging the management, you would care to look at both the pilot and the management in the same light, instead of viewing this as a "lost soul who was getting the job done."
You may also care to look at TC who allows this attitude to prevail in the coastal regions.
Quite a number of these smaller operators are a Type C Dispatch - in other words Pilot Self Dispatch - in some cases the management has written into their COM that there will be an authorization process to weight the risk and make sure pilots are making the right calls - I would suggest that this is not what is going on with this or other coastal operators. I would also suggest that many pilots would despise management stepping into the go/not go decision. So until such time that this happens, and should they be operating a Type C Dispatch, then the pilot gets all the blame for flying in weather below minima as far as I am concerned. You want the PIC, then act like it.
In this case, the only blame management can have (and I stress in this case) is that they did not pull this guy from the flight line and retrain (as you suggest) or amend their ops manual. Either way the final decision in the Pilot-in-Commands.
We all get the tasks given to us done in one way or another, but the safe way is to wait for the weather to pick up instead of relying on some messed up attitude that "...because I've flown in this area for 20 years, I've seen everything and, and, and..."