from an ic standpoint, though. I think that's what you're disregarding here. The Eyes of Silas were an exploratory group if I'm right here. For the most part you have brigands, privateers, more brigands, a knight and rangers.
that isn't the Eyes of Silas
and even then, what happened to the Eyes of Silas- oh, most of them died.
people want more then one ship because they want to lessen that chance, and even more so don't want to deal with their adversaries. [ not to mention we should applaud them because seriously that crap is annoying for the DM's too. ]
and now we get to my fine point here
Riptide ( Two ships that are already confirmed ) = Possible death, ( as baron stated, death is highly likely )
or
we go the Eyes of Silas route= where people have to be lucky like Edward and his buddy to survive, which, as you know, is not everyones normal intentions.
You're talking about a group that, for the most part heard 'riches and exploration' and immediately were down to do it. Some are genuinely down for exploration and I applaud them, but the circumstances simply are not the same and this is not a passive event.
And seriously historically speaking and scientifically speaking any ship that is more then a galleon is going to be slightly difficult to man with the men/power we have
which isn't enough at all.
( the fact we're historically manning a warship with only.. ( well cymkek you should know ) how many men is pushing it )