I record banking and borrowing with two entries per transaction: When I bank points, I record one transaction, as of that date, as a withdrawal, and another transaction, as of the beginning of my next Use Year, as a deposit. Similarly, when I borrow points, I record one transaction, as of that date, as a deposit, and another transaction, as of the beginning of my next Use Year, as a withdrawal. Then, along with my regular allocation entries entered as deposits (which are scheduled for the beginning of each Use Year, entered automatically for me 11 months prior), and my entries for each reservation, entered as withdrawals, it all works out great.