1) Currently you have the choice of 7 different faction types to choose from:
Royal Navy, Pirates, Privateers, Undead, Orcs and Goblins, Dwarfs, Elves.
2) Each has different strengths in different areas represented by their stats and skills they can acquire.
You must decide whether your crew wants to be famous or infamous at the start. Depending on your actions during each game your crew will become more famous or infamous! You start with $500 and can purchase crew members, weapons as you choose. Allowing you from the start to go for a small well armed crew, or weaker with greater numbers.
3) A starting crew will be near 6 or 8 figures depending on cost, and you can have upwards of 30 so long as you can continue to pay them.
4) Yes
5) Cooks, doctors and such fall into the "Special" character category, they can be "hired" after your first game.
6) As I have not yet played Cutlass! I can't say, it has more of a "Fantasy" feel to it with the added races, and the random initiative high jack could become one sided. where as LotHS has a specific player turn. as for Pirates! there are NO rules for ships in Cutlass!
Hope this helps, if I get a game in, I'll report back.