Bootstrapping of stock price (Data based simulation)

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I have a bit complicated problem, and would appreciate all help.

I want to test if companies times the repurchasing of their own shares such that they are relatively cheap. The way I want to test this is by bootstrapping. Imagine a company, A. In 2010 they bought back their own shares in three different occations. The first time, they bought 10 shares with a price of $1.1. The next time, they bought 20 shares with a price of 1.2 and the third time they bvought 30 shares with a price of 0.9. Combined all these transactions had a cost of $62. I want to see how this combined sum would vary if the date varies. With other words: How much does it cost the company to repurchase the exact same ammount of shares divided on three different events randomly throughout the year. This is just an exaple. I have many companies, repurchasing their own shares many times per year. It is preferred to rund 10 000 trials per simulation.

I have no idea on how to resolve this problem. Can anyone help me please?

A.