I think before you do anything you have to ask: Considering the cyclist is a weekend warrior rider, how much $$ do you want to spend on this project? Or put another way, how much money per mile is this worth to you? Even a cassette will set you back a pretty decent amount, but changing to a mountain cassette or switching to a compact double will start getting into the serious money range.
Does he shift all the way down when riding on hills? On group rides I can't say how many guys I've see refuse to shift to their smaller chainring or down on their cassette, so they're really killing themselves on hills for no reason. If he's just trying to be macho on hills, you'd be best off getting him to use all his low gears first, rather than changing anything out.
That said, I have a couple other thoughts, because I actually had this exact issue with my previous bike.
1. Can you just exchange the chainrings he has for smaller ones? I'd check with your LBS to see what they can do for you as far as that goes, because it'd be much cheaper than going with a compact double but get you some good benefits.
2. If #1 doesn't seem feasible, I'd say change the cassette first. It'll also be cheaper than going with a compact double, and it's worth seeing if just getting lower gearing that way works. If so you'll save a good chunk o' change.
2.b. You can also look into getting a mountain bike cassette. These go really low, and would probably meet all his low-gear needs. The drawback is that you probably would have to replace the derailler as well; you'd have to check with your LBS to see what's feasible in that department.
3. As other people have said, switch to a compact double. To do it all the way, with a compact double, it could well be hundreds of dollars (my LBS estimated about $500 to put a compact double on my old bike).
4. He could just do what I did: I kept riding up big hills with the gearing I had, and eventually I got stronger. This option is free and works, but can be kind of painful. (Full disclosure: I later bought a custom bike with a triple and the lowest gearing available to road bikes.)





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(one of many simple rule of thumb to being a good climber).

