Maintenance Schedule Checklist

I am trying setup a maintenance schedule checklist for a large list of items. Each item has a cycle in weeks for the checklist. I set up a nested if statement to check if the item is overdue or done based on the cycle and the current date. The if statement checks when the last time the item was done or overdue and populates an "X" for the next due date. It works fine as long as the cycle is 4 or less. After that there are too many if statements and I get an error. I'd rather not have to use a macro to get this to work. Any ideas?