For Helmsman, you have five applicants of some note:
1) Claude (its a common Talpan name) Margen, a human sailor that is the near definition of typical. Mid twenties, married looking for a good job, several years of experience on several ships having seen minimal combat. Fit and passes all of the basic seamanship tests. Well spoken, calm, and respectable.
2) Marnid Kalmaltou, a young human with Intorian background that is excited and energetic. He has been on two voyages and speaks of the adventure on both, one was a recent corsair ship. He has not been Helmsman before but demonstrates the skills needed. He is lean and nimble, unmarried and ready to go on a moment's notice.
3) Fitolin Selso'anet, a half-elven noble. He comes highly recommended with three letters from notable members of Port Talp. He has a fine education, excellent equipment including two magic items (you note upon detect magic inspection). He conversation is polite and correct at every turn. He demonstrates a superior knowledge of the skill set required. He has been at sea many times, but not yet for a long voyage.
4) Esimato Etumi, a Horarian in his thirties. A long time fisher, he has switched careers. He has a family with three children. He shows the wear of two decades working at sea. He answers are a bit rough an uneducated and he speaks common as someone would that learned it later in life.
5) Marco Ponticelo del Vento is a Nipit whose name Chase and others that pay attention to the famous have heard before, and he arrives at your door. Bordering on flamboyant, he has been sailing the seas for over twenty years; sometimes along on a small ship to demonstrate his skill. He is talented and as skilled in seamanship, and likely more skilled, than any of you. He comes in dressed ready for a long voyage with gear that is top notch and a number of magical items. He is not overbearing when he speaks, and does not come across as if he thinks he is the deities' gift to you and the sea. He is confident, however, and would clearly expect a nice price for his considerable skills.