Helicopter for 60 yr old rich dude
Well, they do say opinions are like a&%*holes; everyone's got one, and as Monsieur FTDK notes, you'll get stacks of advice on rotorheads, but if it's any use to you, here's my tentative opinion, based on the very little little info I have about your boss. (I fly fixed wing and helis, privately, with about 1400 TT fixed wing, 350 TT heli, btw)
60's not too old to learn, per se, all things being equal. Flying helis, like flying in general, comes down to attitude. And that's the real question, here, I think - what is this guy's attitude like? Cos the thing is, people who have made their own money often have a pretty poor attitude when it comes to flying - not always, but often - as they don't necessary understand that the laws of physics can't be charmed, bent, or manipulated in quite the same way that successful business executives can bend social circumstances like laws, markets, and so on. If your man is keen to learn and not overconfident - ie HUMBLE - then sure, I'm sure he could learn to fly a heli, and operate his own, eventually. I would agree about no IFR and no night flying - and would also recommend that if he was going to do it, that he have some sort of "mentor" program going, so he had an old hand to call on, whenever he had some sort of problem or question. Which of course he will.
There are a number of risk factors in flying helis, in my opinion. Being weathy is definitely one of them. Operating privately, without the experience & rules of an appropriate organisation, is another. Owning and operating your OWN machine is another. There are many others which may or may not apply to your guy, but there's three for a start. The gaps can all be filled in with ATTTITUDE, of course, but it's probably a good idea to be careful here. So my answer is YES, he can learn to fly helis, so long as he has the right attitude, doesn't cut corners, and is prepared to put LOTS of time into learning to do it properly. If he sees flying helicopters as an airborne version of driving, he may well have problems at some stage...
Oh, and Robbies? I don't think they're more dangerous than any other helicopters, blade AD notwithstanding. They do require more conservatism than some other machines, primarily cos of the light rotor system, and yes, a well maintained turbine like a Jetranger would certainly be a safer bet than a Rbbie, I reckon. Depends how much money he has, of course - a Jetranger would probably cost four times, per hour, than an R22 to operate, not to mention acquisition costs.
So there's a few random thoughts for ya. Hope they're hopeful...