Jason,
In attachment I added a simple docx file containing a custom numbering.
When converting the document to pdf I noticed the numbering isn't formatted correctly.
I did some tests with the numbering an this are my conclusions:
1. Changing the font type of the numbering works and is correctly converted
2. Bold and italic properties are not converted to PDF
3. When using a custom numbering with a lot of text, the numbering covers ...