Seawolf,
While your question is well thought out, I think you are making a poor decision on even using wire, kinda making the question of the type of crimper redundant.
I replaced my wire lifelines with amsteel a few years back, and would never consider switching back to wire. They are lighter, stronger, don't rip off your hair (remember coated wire is dangerous, dangerous stuff and should never be used on boats), and much much cheaper. Basically my new rope life lines cost me a grand total of $150 for a 30 foot sailboat, significantly less than even a few of the fittings I would otherwise have had to buy. And two years later they still look brand new, no chaffing issues at all, no wear points, no significant stretch, and this is on a hard raced boat.
To answer your question, I don't think there is a real difference in hand and level crimping in terms of safety, so I would go with the cheaper option. And honestly 14X4 or 14X5 crimps either way sounds like a really long day.
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