The problem is the qualities you are looking for in a liveaboard boat are going to be very different from the qualities you'd want in a bluewater passagemaker. If you're just island hopping, you may not need a true bluewater passagemaker, but might want something a bit better than a regular coastal cruiser. It isn't so much that Catalinas aren't reliable, but that they're not designed as bluewater passage makers.
The Catalina would be a better liveaboard, since it is going to have far more accommodations than the Cape Dory Cutter. However, the Cape Dory will tend to deal with rough seas and heavy weather better overall.
I generally recommend you reserve at least 15-20% of the boat buying budget for refitting, upgrading and modifying whatever boat you do buy.
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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.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.