You will need a third-party product because the PDF conversion does not ship with SharePoint unless you count the most basic conversion for MS-Word only, which is available in some editions of SharePoint 2010.
Check out this product , it does exactly what you want, including the checkboxes in Service Pack 2 (SP2010), and can be used through workflows and web pages for service calls.
Further information as well as real-world examples can be found here .
Disclaimer, I work for this provider, so this is a shameless plugin. However, it answers your question :-)
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