QB Issue Resolution:

So I figured out a solution, I setup an app specific password for Quickbooks via Google admin and setup the email manually in Quickbooks. Looks like Apple Script was having the issue somehow.

Resolution for Issue 'Invoice Emails Not Sending With Outlook' available: Yes (Solved).
Source: Intuit Community forum.

Invoice Emails Not Sending With Outlook: this issue or error code is a known issue in Quickbooks Online (QBO) and/or Quickbooks. Support for this issue is available either by self-service or paid support options. Experts are available to resolve your Quickbooks issue to ensure minimal downtime and continue running your business. First try to resolve the issue yourself by looking for a resolution described below. If it is a complex issue or you are unable to solve the issue, you may contact us by clicking here or by using other support options.

Support for Apple Script
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