So, ever since the sail system was added I've been a pretty big enjoyer and proponent of it. However, some time spent doing this has led me to see some pretty glaring cracks in the system.
Firstly, the only true requirement for sailing a ship effectively should be the sail skill. I know that there are plenty of people who would love to get in on sailing, but even if you've bought a full investment of sailing skill, that's not enough. It's not even enough to have a full investment+gear AND working skill focuses into your build, normal AND epic variety. It's not even enough to have four other people with you who have done the same thing. You NEED a bard, to hit the sail cap for your ship to sail in pve alone, to say nothing for pvp. You also NEED a carpenter/tailor for repairs, which I might add are some of the rarest professions around. These mandated requirements lead to people coordinating things OOCly, asking their friends to make a bard or to take carpentry/tailoring as a craft if they don't have one already. It's very hard to get this done through IC means alone and at the very least favors people who can lean on friends to make a sailbeast bard to get everyone at or near 100 sail skill.
This could be fixed if the bar for max average sail could be lowered to a sane number, attainable without a bard, and if repairs could be done with sail ranks instead of carp/tailoring. More types of people could be included, a bard becomes a comfort option rather than a requirement.
Secondly, speaking of gear: I think this could bear getting looked at. Fitting a +2 to skill on all your gear is doable. It might be more difficult for some than others, but it is doable. However, putting the optimal +1 to wis on every item is less so. This leads to people having to spend not only the money and effort of getting a full set enchanted/bought, but to invest (precious, for str characters) inventory slots on a "sail set", which is 11 inventory items, some of which are large like chest armors and cloaks (4x4) and boots and helms (2x2) as well as gloves (1x2). As an aside, having a bunch of people standing on deck with a dagger in each hand looks dumb.
Without feats, sail blessings from rituals, and with max gear, the most your average sailor would be able to run is 68, plus (or minus) base wis mod. This is WITH owl's wisdom and WITHOUT a bard.
If you don't have the (expensive, rare) +5 sail items, the number becomes 61. Maybe 63 if you compensate by adding more wis somewhere.
I feel this is the number that should be balanced around, NOT the maximum 100. Something around 80 average or so would account for a bard, ESFs etc. as far as bonuses go, and it is also very attainable without going to extreme means.
If the number is lower, then the bonuses from blessings, skill focus feats, having a bard, having good gear etc. actually become MORE meaningful, not less, because these are things that make you valuable to a crew because you bring the average up from just the baseline. They're things that make you "a great sailor" rather than just "a sailor." Overall I feel the required average sail should be looked at and discussed; lowering it would make it easier to include more people, and in an organic sort of way.