Hi Franklin Ward,
I'd like to ask you several questions first to narrow down the issue.
Are you using an Exchange account? What is the error you got when you click to open Outlook? It's recommended to post a screenshot here.
Are the files and pictures in your computer's store lost? Or those in your thumb drive?
Regards,
Beverly Gao
Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.