When you click on the send to to send a picture, does the resize window pop up? Also, try the send to when the email client is already open, and see if it works then.
Confirm Outlook is set to default using this method?
Start> In search box type Set your default programs> Enter> Select Microsoft Outlook> Click Set this program as default> OK
You can also try this
Start> In search box type Default Programs> Enter> Set program access and computer defaults> Click on Custom> Select your mail client> OK