I have a couple high rides, also. My favorite is my HBE Com III that picked up about four years ago. Fine holster.
As for my opinions regarding why high-rides were first developed, and their relative strengths and weaknesses - take it with a grain of salt you know how opinions are
Like your friends, I also sometimes choose a high-ride if I'm wearing a sweater, the garment is less likely to creep up over the top of the stocks with a high ride.
All holsters are choices. Everybody should own a high ride because they offer something distinct from other ride-types - and the clothes you wear on a given day make a huge difference as to which holster is the better choice for a given day.
My .02 (with the deflated dollar, actually now .078).
[THREAD HIJACK]
Does your wife ever shoot your Cougar? I"m thinking about taking my wife shopping .... opinions ??