I have a pair trading strategy with positions that last 3-5 days and trades 2-3 times a month. By design, all the trades are profitable until the cointegration is broken.
Should I calculate the Sharpe ratio with daily or monthly returns? (annualizing afterwards in each case)
With monthly returns, most positions will be closed so I will have mostly profits (and maybe a loss if there's an open position at the end of the month).
With daily returns, I will have partial profit and losses each day.
I haven't done the calculations yet, but seems to me that the annualized Sharpe ratio of the monthly returns will be higher than the one with the daily returns, even with the difference of the annualization factors $\sqrt{12}$, $\sqrt{252}$ respectively.