Another Cat Sailing Jarhead here (8654). Congrats on your son's choice. He's with a great group of men.
A few years after I got out of the service in 1969 I bought a new Hobie 16. Sail number 10822. I had that boat until 1984. I bought a NACRA 5.8 and never thought about the old Hobie again. In 1999 I bought another Nacra 5.8 and still sail it regularly. I'm teaching my son the ropes (sheets?) and passing on knowledge.
When I was a little younger I would sail all weekend in heavy weather, get wet, get tired, but when I went to work on Monday I felt great. Now that I'm a bit more seasoned I can still do the get wet, get tired thing, but on Monday morning I can neither lift my own coffee cup to my lips or feed myself. I would like to find the person that called these the golden years and stomp on him with my titanium hip joint until my by-pass gave out.
I'm gonna get me a big fat monohull with a round butt and teach my son to sail that. (Once I learn). I just gotta believe that at this point I would rather sit in a nice snug cockpit with a fat bottomed wench and sip rum rather then hang out on a wire in 20 kt. winds taking salt spray to the face. Besides, my Speedo's are getting a bit tight.
Careful of burying a hull on the Hobie. They can go from 15 knots to zero in about two feet. You will launch off the trapeze, play maypole around the mast and end up with your feet pointing skyward while you're stuck to the jib. All this happens just before the infamous turtle exercise.