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I mean, if you are able to travel at warp speed, you should be able to come up with a viable calendar.
What canon information is there regarding whether or not somebody boldly fixed the Leap Year flaw that Earth currently uses to reset their calendars?
It would seem that yes: there are still leap years
Memory Beta doesn't have much to say on the matter unfortunately.
According to Memory Alpha:
One Earth year was equal to 365.2425 Earth days in the Gregorian calendar. To compensate for the fraction of a day, a leap day was added to every year whose number was divisible by four, unless it was a century, unless it was divisible by 400. These leap years consisted of adding an extra day to the month of February. Instead of the usual 28 days, there would be 29.
Now, this explains the situation as it currently stands; because there seems to be no mention of removing leap years, we could assume that they still exist.
Furthermore, the introduction of Stardates did not impact our local Earth calendar:
Stardates did not replace clock time or everyday units for expressing larger timespans, such as days, weeks, months, years, centuries, or millennia
Hence, it would seem that there has not been any modifications made to our current calendar system in the Star Trek universe, at least none mentioned which would impact the presence of a leap year.
