The level of planning ahead you do so that things are in motion around the PCs, in their immediate vicinity or in farther off parts of the world is up to the DM to figure out based on the speed of the game and travel.
. . .
If I am understanding and the idea is "here is what this group is doing in the foreseeable future" then just set it up so the world doesn't look like it is waiting for the PCs. Let things happen as they were intended, and let them change when the PCs cause something to interfere with that "plan". Then with the PCs there the plans change, and after the PCs leave a continue set of advanced plans for this group can be made to let you know what this group is doing at all times, should they meet up with the PCs again.
Nod. I basically do this stuff in my head for several important factions and NPC's. But I don't write down most of it, because I think of better nuances and connections and influences between PC's and NPC's actions as we go along. Plus there's the whole "if the PC's get interested in this NPC, this NPC needs more background, motivation, and plans than you originally thought of, so figure them out". And there's the "so we meet again, time to wing what the NPC has been up to, if it matters". Part of the joy of DMing is making the world seem real and dynamic.
I guess this tool might help, if it's allowed to be interactive wth the PC's interests and actions.