Galleon - Can still be outran by the Brigantine with crosswind.
Sloop - Has a greater speed with sails adjusted perpendicularly to the boat while there is some potential wind over actually "catching" that potential wind.
All ships - Faster with sails adjusted perpendicularly to the ship than to either side, when there is no wind.
Whether these are strategical choices or not (ahem, I don't think Rare actually believes that boats go faster when the wind is pushing them backwards), we've still yet to see any sort of acknowledgment on these fairly huge problems. Someone might go as far as to mention that maybe the Brigantine should be faster than the bulky Galleon when catching wind on either side, but I can tell you that's probably not intended, just as all the other problems. The result? Pointless chases across the map that could've ended as an awesome ship battle that declares a winner. Instead? I'll just ram my boat in yours to make sure you don't dust me behind because the boat speeds are ludicrous.
Any thoughts welcome :)
