welcome to the community!
I know that you are looking to solve your task with the out of the box functionality, which may be possible, but also troublesome at times! Have you thought of looking at applications yet, that allow easy compilation of dyanmic tables in MS Word, and also easy formatting? dox42 for example allows to easily set up repeating tables in Word templates, and the formating is done with MS Word functionalities you are familiar with, so creating headers and formating columns is easy. They even have a sample template with a repeating table that allows you to connect straight to your CRM system - so you could use it and you are ready to go with your template: https://www.dox42.com/Resources/Sample-Sales-Quote
Hope this information helps,
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