thechosen0ne: the vacation system was changed a while ago, and the whole flag has no meaning anymore.
Everybody's vacation works the same way, and there is nothing you have to do (or could do).
As was explained, whenever the first game runs out, all games get an extra hour, and your vacation time is reduced by an hour. Also you have two 'weekend days' which by default are Sat and Sun, but you can modify them. On those days, you do not use up vacation at all, its free.
If you have enough vacation left, you don't need to do anything, just go in vacation. If you have not enough left, nothing you can do.

The difference for non-paying and paying members is the total amount of vacation you get on Jan/1: Black rooks get 40 days (this means 8 weeks, as only five days a week are needed - see 'weekend' above), and non-paying get (I think) 10 days = 2 weeks. No roll-overs, just everybody gets reset on Jan/1 to his current membership's amount.
I hope that helps you!

Oh, and about the -2 minutes: The timer demon comes around every ten minutes. Until then, the remaining time just keeps counting, so might end up with it showing up to -9 minutes. That does not matter to you, the timer demon applies your vacation (as explained above) before it times you out.It's the same program, so it can't happen the wrong way around.