Yeah, this is a limitation of the mapping library I'm using, since it doesn't "infinite scroll" the maps. I believe it's on their roadmap.
But thanks for the suggestion, I have something like that on my mind, where if there's one point to another point, and it intersects the date line, turn into that into 2 separate segments, so from p1 -> dateline, dateline -> p2. I just haven't quite done the research or looked into the math to determine whether there is a crossing of that boundary, but also, getting the coordinates of where it's intersected, to draw that out.
On a quick search I see https://gis.stackexchange.com/questions/83425/splitting-linestrings-on-dateline-with-openlayers
But any other suggestions on an algorithm would be great. We can discuss it on Discord too. I'll probably end up doing some research about this over the next few days to finally get it off my list