Option 2 is better if just consider the enterprise

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Option 2 is better. If just consider the enterprise value , option 1 is better than option 2. You can find the figure in below excel. But, after considering the cum deficit, you will find option 2 will bring positive cum deficit number. And enterprise values with option 1 and option 2 are very close. So, option 2 is a good choose.
What are the tradeoffs?
the Free cash flow will be less than that using option 2. it will face more risk. If the new company (pinkerton +CPP) wants to increase its market value or stock price, option 1 should be used. But if the new company wants to be healthy and stable, option 2 should be considered. Because after paying off debt, it will have more money than that under option 1

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