The way you're thinking about it, yes -- but the passage of a month may take you from December the [mumbleth] to January the [mumbleth], which are in different years. For some strange reason, code in the wild doesn't always account for that, so the due date for an item may well be eleven months before the request was entered.
If the tests are failing because the production code is confused about daylight savings time, then you may have a serious problem.
If on the other hand it's just the test code that's flaky, usually such problems can be alleviated by refactoring such that one passes the time function as a parameter. This is in preference to hard-coding calls to the system time in test, which imho one should never do.
Once an arbitrary time function can be passed as a parameter, one can provide a mock or fake system clock for test purposes. Ideally one would still want to test under daylight savings' conditions. But at the least this approach leaves one in a place where one can test the common 24-hours-in-a-day case without having the tests spuriously fail two days out of every year.
Between 1582 and 1752 England had two different New Year's Days, January 1 and March 25, used for different purposes. The same day had different years depending on who you were talking to. See http://en.wikipedia.org/wiki/Dual_dating.
