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In all likelihood the issue is with the size of the photo (not actual dimension - size in this case refers to size of the file in megabytes or gigabytes.) If you can make the photo smaller, that will do, because Live mail probably has a size limit on the types of files you send.
Open photo and then go to menu. Go to more items and then crop the photo. You have to resize the photo and then save it. Send the message again with the resized photo and it should work.
If its text message then you need to click the link which should open your browser and requires a user name and password from the service provider. If it's email pictures then you need to download them separately. by clicking the attachment. HTC mail usually shows more content from an email than the gmail widget does.
I'm assuming your sending the picture by bluetooth. The Hero's software unfortunetly is not capable of recieving pictures by bluetooth. And it can only send pictures using certain programs off of Android Market.
There is no infra-red transfer and the phone has a very crippled form of Bluetooth due to the chipset fitted which means that the Hero is physically incapable of sending pictures or any other files via Bluetooth. There are no apps, firmware or forthcoming Android updates which can fix this as it is purely a hardware limitation. Bluetooth on the Hero can only be used to pair up with car kits and earpieces, but even then it's totally incapable of Bluetooth voice dialling due to the same near-useless chipset.
The Hero is a superb device, but you've hit on one of the few really annoying flaws in the design of what could have been a real iPhone alternative.
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