When printing withing Data Driven Pages, each page should spool by itself instead of all the pages spooling together. Granted it is nice to see 1 file in the queue, but when there are memmory limitations, pages at the end are dropped and not printed at all. This is also the case when exporting the series as a single PDF. They should export each individually and then merge them so they don't all need to be retained in memmory and cause the entire process to fail when the size is too large.