There are several issues. 1. If others are going to use this document, ensure that you change the font on your userform to a standard font, for if the font is not available (it's not here) the display is truly dreadful. I have made some changes

2. The issue with populating the bookmarks is frankly never going to work as you have it. Better to assemble the values from the userform and write them all to the end of the document - addressed!

3. Check boxes make more sense than list boxes for yes no choices.
4. The code for opening the document needed some work.
5. And most important of all, if you want to repeat the data, you can't run a command from the form if you have already unloaded the form. Much better to run the code outside the form as shown in the attached.
I think that should get you started