Could be that you will be able to buy tokens cheaper from a bounty dump but could also be that it will not go under ICO price. If you are really unsure you could try to invest half of the money you want to invest now in the ICO and the other half you could try to grab some cheap tokens after the ICO has finished and tokens are on trade.
Yes, that is something I always advise people to do aswell. That way you dont get the bad FOMO, which sometimes makes u do stupid shit. And you also still remain the chance to get cheaper tokens from the free market. It's always a good way to act.