Questions for Cake Decorators - When to Decorate?

I did my fondant cake 4 days in advance with store bought frosting underneath (i used store bought because I figures the hydrogenated fat would keep better than real butter). Painting fondant in advance poses some serious problems since you have to contour it onto the cake and smooth it out. You can however make fondant and keep it air tight unrefrigerated for a month. Your weakest link is the buttercream. My fondant remained playable for 4 days (and would have gone longer). Figure out how long you can have unrefrigerated butter cream and thats your answer. The frosting will keep the cake from getting stale as well as keep fondant soft. But as for us, we are in a heat wave, so all bets may be off if thats the case. None the less, I got away with 4 days and you probably can too. A ribbon to finish the base hides a multitude of imperfections.

How about making pastillage tiles to paint on. Then you can paint and attach them whenever.

Yup. Vodka. Goldschlagger can be fun, too, if you want some sparkle, but I prefer pixie dust and vodka for detail work because it doesn't get bumpy the way goldschlagger does.

Ha! You ruled out my first thought (rice paper transfer) :P

Second thought would be more of an applique technique + freezing

Cut out the silhouettes of the players from rolled fondant. Keep them individually in the freezer in ziplock boxes when you aren't working on them. Then, drape your cake with a single sheet of fondant, butter cream or wet the backs of your painted players, attach. Then use some Dragée or piped frosting to outline so the edges don't look stupid (for lack of a better term).

Gum paste, or modeling chocolate might work as well. But I've never done detail work on either. So I'm not sure.

I'd be REALLY worried about using your base fondant to paint ahead of time. But then, I've yet to lay fondant without it stretching. I would think it would warp the paintings. Possibly if you had cardboard under each face for the transport, then slid them out as you laid it down... but I'd still be worried. Plus, it will be a stone female dog to keep in the freezer or fridge wrapped up.

Some cupcake hockey pucks (or hostess ding dongs) might be pretty cool, too.

If I were you, I would frost and fondant tomorrow night, keep it in the freezer and then start the portraits as soon as possible. If you can only do half of them tomorrow and then finish on Friday it'll be ok. The last showpiece cake I made I took three days to do it. (Four if you count the day I baked the cake.)

And yes, vodka is the best medium.

I would go over to bakerella and ask her! Some pro is bound to give good advice.