Ooh, I like the idea of a prelude adventure, and will probably steal yours, Fiendish Dire Weasel. What I might do, though, is start everyone out as one of the NPC classes (adept, aristocrat, commoner, expert, warrior) and tell them they can only spend skill points on naval skills (broadly construed, so that balance and climb count). We RP for a bit and then run an attempted pirate attack (give the captain of the PC's ship lots of ranks in profession sailor and put the PCs in a faster boat to put the odds in their favor). After this prelude, they arrive in Sasserine and "level up" to first level regular PC classes. The captain sells the ship, pays everyone the max for the starting gold for their class, and leaves them to their own devices. PCs get skill points for new PC classes as if they were first level characters (so x4), and can put the skills in anything they want (we'll say they were practicing/studying those skills in their spare time on the boat and it just now all catches up with them). That way they'll get a few extra hp, some extra skills, and some extra money to spend at the beginning. Bam, an extra leg up, but it doesn't feel like they got it for free.
Has anyone ever done this before? I guess I'm trying to come up with the equivalent of starting with 0-level characters that cropped up a couple of times in 2nd ed.
I also have Stormwrack, and you make a good point...when else are you going to get to use it??
As for the free feats, maybe what I'll do is PCs who are from Sasserine will get their special feats, and everyone else gets a free skill focus for one of their maritime skills. Again, it's something that's so specific that shouldn't be overpowering, but should also be at least kind of useful at some point.
I'll probably go with the 28 point buy, in that case, like Paolo suggested. I usually like rolling dice, but in this case I'm playing over the internet and one or two of the guys I don't know very well. Point buy will help avoid any cheating problems.
I also will probably institute your house rule, Cthlulu, and provide the caveat emptor at the beginning...
This is going to be pretty sweet.