Requirements: User needs a workflow that based on review date it will send an email 30 days before and 15 days if it has not been completed. Needs to take the approved document convert it to PDF and then move it a different location. Once it is approved it needs to kick off again 365 days from approved date. 

Solution (Attached): I currently have it working fine by using a state machine and a pause until action at the beginning of the workflow. Just not sure this is the best way to do it for performance and such.

Question: What is the best practice for running such a workflow. Should it be a site workflow that kicks off a list item workflow? Is it okay to run as an endless loop on the item? What are the pros/cons of each?

Please provide some insight in to what the site workflow should look like to kick off the list item workflow if that is the recommended path.