How do I send messages to both mobile phone and email at the same time?

You should find that this is possible:

1) Goto New -> Text Messages
2) Click on ‘To…..’
3) You should have 2 sets of Address Books available:
Outlook Address Book – This is the normal address book for sending emails
Mobile Address Book – Contact for send SMS messages

After you create an Outlook Mobile Service account, a Mobile Address Book is created automatically. This address book contains all the contacts in your Outlook Contacts folder who have their mobile phone numbers listed.