Hi,
For a start those question marks mean that the document linked to could not be found - maybe it has on content or isn’t included?
As for where the page numbers appear, you just need to adjust the ruler in the contents page to tweak the tab placement. Entering page layout view is a good idea for this.
All the different auto-number types can be found in the Edit > Insert > Auto-Number menu, but the tag for uppercase Roman numerals is <$R>.
Hope that helps.
All the best,
Keith