My problem: I recently booked a business trip about three months out, noticing slightly too late that there's a huge event (Formula 1 race) happening in town the previous weekend and all the remotely convenient and/or comfortable hotels are asking crazy rates (US$500+).

The usual rule of thumb of booking flights and hotels is the earlier the better, since prices usually go up but rarely come down. In this case, though, I have a sneaky suspicion that hotels may be demanding too much and there may be a fire sale of unsold inventory right before the event.

So should I take my chances and hope for the best on HotelTonight & friends on/just before arrival? Or should I bite the bullet and pay lots now, to avoid having to sell a kidney if rates go up even more? (And no, I can't change my travel plans.)