I use a similar progression to later seasons of TNG and beyond, where Stardates sync up with my own calendar as the year progresses. For instance, I started at the end of 2017 and decided that was directly after the end of the events in Nemesis, which was at the end of 2379. Now in 2018, I’m playing in 2380, and the Stardate progresses through that year (57xxx.x) just like my own calendar.
You can do the math manually, dividing a year into 1000 equal parts (it turns out 1.0 is roughly equal to 8 hours), or you can cheat like I do and use a pre-built calculator. I use this old Stardate Calculator, which tells me that the current date and time in the year 2380 would have a Stardate of 57250.2. That checks out – April 1st is almost exactly a quarter of the way through the year.
I like the dates progressing through the calendar year, because it shows two things. One, the downtime between adventures isn’t empty – stuff happens. If we delay a week, the Stardate is a week later. Since the USS Thorne is on a 6-month mission of science and exploration right now, it’s great to recognize that only a dozen or so of those dates are truly fascinating and worth an episode – the rest is “boring” time spent doing regular work in various star systems.
Last time we skipped a session, I said it took two weeks longer than anticipated to get around a nebula. In the next session after that, the nebula featured in the plot as it held a hidden confederacy of warp-capable species. The passage of time, as measured by Stardates, and incorporated into stories, can help make it all feel more “real”.