There are several ways to handle this successfully. You are correct that bookmarks are easily deleted - especially if you edit the document directly, but if you create a VBA userform (your suggestion 2) to collect the data for the first page - see
http://www.gmayor.com/Userform.htm - then you can use the FillBM function from my web site to write to the bookmarks in the document, both on the first page and wherever the same data appears elsewhere in the document. This method, and the use of document variables (also shown in the link above) are both practical approaches.
Or you could use mapped and linked content controls which require no VBA programming expertise, but are a little more complicated to insert. They do however have the advantage that whatever you write in one of the linked controls is repeated in the other(s).
To facilitate the insertion and linking of controls see
http://www.gmayor.com/BookmarkandVariableEditor.htm and the content control version which appears towards the end of that page.
See also
http://gregmaxey.mvps.org/Repeating_Data.htm