I think the amount does matter. It is that, I don't see big money pouring in Bitcoin market as bad. It is an investment and brings liquidity to the market. The bigger the fund getting into Bitcoin is, the more liquid Bitcoin is. And I think we should not worry about the money leaving out of the Bitcoin market sytem. If it leaves it only means that there is a bigger funds coming in because it needs a bigger fund for that big money to exit with profit.
As your given situation, the amount of money inveted practically matters because Bitcoin will not surge if the investment of the coming people is too little. But if the incoming investors invest a huge money then we can see Bitcoin market surging. So it does matter to fulfill one of your statement and that is to sell higher than the amount we invested.