1 - Yes but why not save the complete coverpage as a coverpage building block and insert it in your document (or not) as required following the examples used by Microsoft.
2 - Yes - you can process any images as required.
3 - Not as long as the relevant ranges are addressed. A table is a sensible way to layout the types of header (or footer) you are using. You can write to any part of the table using a macro.
4 - What does this mean? What image? If you mean they different versions of the header and footer for landscape pages v
is-à-vis portrait pages then again use building blocks to hold the appropriate headers and footers and insert them as required. However see http://word.mvps.org/FAQs/Formatting...apeSection.htm (but see it quickly as this page will only be available for another week - as the mvps site is shutting down).
What is not clear is how the checkbox is used or even where it is located? There are no macros in your document, so it is impossible to judge how you are using them.