QB Issue Resolution:

best answer I can give you is maybe

after you upgrade, check to see if the attachments carried over, if not use this article (book mark it now so you can get to it later)

http://support.quickbooks.intuit.com/support/articles/HOW19567

Resolution for Issue 'I am about to Upgrade from QuickBooks Pro 2014 to QuickBooks Enterprise 2015. Will my attachments carry across with the imported data or will I lose the attachments?' available: Yes (Solved).
Source: Intuit Community forum.

I am about to Upgrade from QuickBooks Pro 2014 to QuickBooks Enterprise 2015. Will my attachments carry across with the imported data or will I lose the attachments?: 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 attachments
Quickbooks Repair Pro will resolve it efficiently and affordably. Guaranteed resolution of your issue, or you pay nothing!

Error Recovery for attachments [Canada]
E-Tech is the #1 Quickbooks data migration and Conversion service provider.

Get 50% off Quickbooks Online

Click Here for 50% off!

Additional Support Options: