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It complicates your Operating Agreement a bit, but what you would need to do is to draft your capital account and allocation of income, loss, and distribution provisions so that basically each investment deal is a separate division within your LLC so that separate capital accounts and allocation provisions are maintained for each deal separately within your one LLC and then consolidated at the end of the year to allocate the totals to the respective members. On the members' ownership percentage interests on the tax return, you simply put "various."
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