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Banking
This sounds to me like what the OP was asking for is not possible...
I have a similar situation, where I have multiple transactions on a credit card. At the end of the month, I get a monthly summary. I would like to enter this one monthly summary as a bill, and then to be able to individually select the transactions on my credit card feed to zero out the value of the bill. But I can't do that, unless there has been some update to QBO that I'm not aware of.
Right now, I do create individual expense entries for each transaction and it matches with my credit card feed just fine. But I was hoping to be able to do what I described above to save some effort. Creating a bill and manually "making payment" for the value of each individual transaction does not save any effort compared to what I do now. It would be nice if this were possible.