Little bit behind on where this driver is up to... From the last few posts, have you managed to get dates displaying? I grabbed the driver using the list in the OP and it is displaying as "In 2 days...", would prefer the dates, like you had in your original screenshot. No pressure if you are still working on it, was just curious on where this was up to. Great job getting it going.
I see that you output the date for Calendar entries >7 days out, but in X days for those <7 days. I prefer to see the date myself for each one. I started playing around a bit with the code, starting by showing the date for everything except today, then messed around with the format. I prefer something like my screenshot below. What do you think?
It really comes down to personal preference and I know it is hard to cater for all of those preferences. I can't think of an easy way to account for different options, only to toggle between the current setup you have developed, or "Always show dates". Then the date format could maybe be a preference setting to override the default you code into the driver? I have setup a driver myself that I use on dashboards to format the current date and time, happy to point you to it if you are interested.
I'll understand if you don't want to change the driver, it's a minor thing and something I can cater for myself.