You can run the connector as often as you like, we recommend at least once a day either in the morning or last thing at night.
Is there a recommended way to use the connector?
The accounting connector for ServiceBox was written to allow two ways of synchronization between your accounting file and ServiceBox of customers and if using QuickBooks, job sites. However, we recommend that customer data be maintained in ServiceBox and updates synced down to your accounting file. This will prevent issues with changes being done in both systems and potentially being overwritten during the sync process. In the settings screen, you can turn off the sync of customers from accounting to Service|Box by un-checking the 'Add/Update customers from accounting to ServiceBox' checkbox in the Export Settings tab of the settings dialog.
If you are new to ServiceBox, a great way to get started is to upload your customer information from your accounting file into the system. You can turn on the setting discussed in the previous paragraph temporarily so that customers will upload into ServiceBox and then turn it off, maintaining customer information in ServiceBox and syncing it with accounting.
If you are new to using the accounting connector or just want to have a little more control over what gets into your accounting system, we recommend that you turn on the 'Preview customer actions before importing into accounting'. This will give you a preview screen before any customers or job sites are imported into your accounting system, allowing you to see what is about to happen and choose which actions you would like to happen.