On those further out tasks, are there predecessors that need to be done before those tasks are ready to start?
And do the team members have the filter on Home for "Not Ready" tasks un-checked so it only shows what is actually ready for them to start?
I have a lot of recurring tasks built out for the year for myself (weekly, monthly, and quarterly tasks) and keep my Worklist narrowed down by using predecessors so next week's task isn't ready to start until this week's task is complete. So by showing only the tasks that are ready to start, it limits what shows in that list.