After a long lapse in regular gaming, I roped a group together and laid out all my indie games and threw out a few ideas for what we might play.  It rapidly settled out to everybody liking the idea of a pirate-ish swashbuckler game using TSOY and we moved on to coming up with a rough setting outline and some characters. 

Jay wants a character who's gone his whole life getting the crap kicked out of him, so now he's sooooper tough, with a Secret to that effect.  We came up with this:

Secret of the Survivor
    either +1 armor when using Endure
    or +1 armor against physical attacks
    or +1 armor when using Endure against physical attacks

This is the first experience any of us have with TSOY, so we aren't sure which version is most appropriate. 

Bobby wants a carousing, charming sort of rake who's always making a fool of himself.  We came up with this:

Key of Embarrassment
      1XP when you do something foolish
      2XP when you are ridiculed publicly
      5XP when your embarrassment causes you great harm

That just seems too generic and wishy-washy.  I'd appreciate advice on how to punch it up.

One other thing:

Everything else. When the Key comes up in play, gain an experience point. (You can use this three times per session. This applies to all Keys below.)

The Secret of the Survivor looks fine. I'd use either +1 armor vs physical attacks or +1 bonus die with Endure. I like the latter better.

The Key of Embarrassment isn't so bad. How about:

1 XP when you perform a public faux pas; 2 XP when people above you in status ridicule you publicly for a faux pas; 5 XP when you perform a faux pas so bad that it causes you and your companions great harm.

How does that three-times-per-session rule apply?

Excellent.  Thanks a ton, Clinton.  We're really looking forward to playing.  :)

Actual Play post is here.