Interesting debate. I'm another businessman / pilot in the danger zone of 41yo and 102hrs rotary, and probably like all the others consider myself conscientious, cautious and safety minded. I had the luxury of being able to employ my instructor (1200 hrs TT), whom I thought was excellent in terms of flight skills and airmanship, on a full-time basis to fly our company heli when required.
I think one thing that is at issue with businessmen flying is the transition from business head to pilot head. There are definitely occasions after a bruising meeting, where the mindset is not suitable for immediately taking to the skies. Our pilot almost always comes along on this type of trip, sits in the left seat and gives me the luxury of deciding how much of the workload I want.
He also treats each trip as further instruction, and as my confidence in handling the machine increases, he increases the challenges accordingly ("Practice Engine Failure - Go") etc. I know I'm really fortunate with this setup, but it is definitely giving me a focus to continue to learn.
There are, however, some PPLs who have approached me for SFH on our machine, and having flown with them, wouldn't let them loose on their own in a million years. I definitely agree that an hour every couple of months doesn't constitute currency in rotary, and for that reason alone, the really occasional recreational pilot is in my opinion always a greater risk.
FF