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I don't use the standard messaging app the phone came with so I am not sure if it does what you are looking for. Handcent app does though. In Handcent app you open the compose screen and just hit the plus sign on the top right and go to your contacts and make checks next to each person you want to add. In gmail I don't think you can do this, but I might be wrong. I just type their names, enter, another persons name, enter and so on.
I had the same issue regarding emails and text sent to multiple recipients. I found it a little strange that such a feature was not available since it has long been a staple on other non-smart phones. The Handset SMS app works great! All the functionality that I was looking for.
I overcame the e-mail issue by creating distribution groups within g-mail. Those then are available through the phone.
I also had trouble saving pictures from text to the phone but realized that if you do a long press on the picture while viewing the text in either the original message app or in the Handset sms app, an options menu appears.
Ok, here's what you do, open the native messaging (instead of choosing contacts) press Menu and choose "compose" start typing the first name, you will see your contacts, choose the one you want. Notice the "To" Field, touch behind the name, start typing the next name and continue this until you have all your names that you want in the name field.
in the block named to start typing name, choose the contact then place a , (comma) and begin typing the next person the address should pop up like the first one