I get the feeling he's coastal cruising, weekending or daysailing, not sailing the tradewind routes.
That said, yes, if he wanted to do the tradewind routes, then a heavier light-air sail would be a good idea.
Also, some boats don't go downwind all that well, since they can roll and pitch and otherwise end up handling pretty squirrely.
__________________
Sailingdog
Telstar 28
New England
You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Captain Malcolm Reynolds, Serenity (slightly edited)
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