I never hand out cash. What I usually do is: I hire a new player (that way he had to talk to me and I can determine if he is able to RP the basics), then I tell him that the mission might get dangerous and he'd need better equipment to survive.
Next step is: I go equipment-shopping with him. After this and the job done he has up to date equipment and knows what to do with his ship for a living.
If there's interest I include a small lesson about basic skills fitting to his ship afterwards in Conn.
Although this is much more demanding than just handing over cash, I feel this is the right thing to do since it includes vital information and opens up horizonts. Also I can be sure to support the right kind of person, since I get to know him in the process.
' Wrote:for those who missed it: the moral of it all is ----> traders with teeth are fun for pirates. - within reason.