If “prepaid” rent is received in the prior calendar year, shouldn’t management fees associated with that rent in the current calendar year be deducted from the income in the prior calendar year as well?

Regardless of when rent is paid, we only apply management fees once a month. This means that there may be scenarios in which residents “prepay” rent in the prior calendar year, but we do not assess management fees until the current calendar year. This means that the total income (prior to deduction of management fees) will appear on the prior year’s 1099-MISC.