According to me, the amount doesn’t matter.
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.
I don’t get the point what you are making us understand about the last man standing thing. Bitcoins are like assets, which you will pass onto people at comparatively high price. You buy the Bitcoins when they are low, and now you gonna sell them when the price increases. How does here you the amount of money invested practically matters? No one will left out at the end, as Bitcoins are limited in number, and it will become more valuable in the future. So just buy as many as you can and sell and get the profits.
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.