A friend is in jail on grounds of overstaying and working illegally. In Feb 2002 he exited for Canada and was granted one month when he came back in the US but he filed for extension previously and got approved till July 2002. He's never overstayed before but did work. Is he overstaying based on March or the July? When is bail posted? Does he need a lawyer immediately for the bail procedure? Is it true it will make it easier if you have a lawyer to represent you right at the beginning? Or do you need one "only" when you appear in court for your first hearing? Many advised to save money not to hire a lawyer for the
bail procedure but we're torn in making sure it is the right thing. If he signs a voluntary departure he needs time to settle his affair at least a few months?Can he be granted that? Is he still allowed to come back to the country?

My best guess is that it will take a while before
he can be deported on the ground that he violated his status by working illegally.Once hearing is made obviously there is the need to get a lawyer,from the bail out thru the end.
A pre 9/11 scenario on the case may mean that he can be in jail or on bail for a while as it take sometime to have the hearing of the case.
A post 9/11 scenario is a zero tolerance policy of INS,that they expedite cases that would cause damge to INS reputation,hence the case maybe heard right away and no more time for a month or 2 as you were saying to do unfinished business.
Hope things will turn out well.