Hey Cmdr007,
Welcome to Apple Support Communities. It sounds like your iPhone isn’t allowing you to send iMessage in a group chat but will work when sending to individuals. Group messages can be fun and effective and I'd like for you to take advantage of all the features available in the new Messages app. I see that you've attempted a few troubleshoot steps to try and get it working normally. If you haven't done so already, you may want to try and leave the group conversation, restart your device and attempt to rejoin the group and send a message. If that doesn't work, try deleting the message thread completely and creating a new message with the same recipients. This should clear out any conflicts preventing iMessage from working properly in the group message thread.
Here's a resource that can help:
Send a group message on your iPhone, iPad, or iPod touch
Specifically, use these steps:
- Open Messages and tap

to start a new conversation.
- Enter the recipients' names or tap

to add contacts.
- Enter your message, then tap Send

.
To send a group MMS message on an iPhone, make sure MMS Messaging is turned on. Go to Settings > Messages and tap MMS Messaging. If you don’t see an option to turn on MMS Messaging or Group Messaging, contact your carrier to see if your plan supports Group MMS Messaging.
To leave a conversation, tap Details, then tap Leave this Conversation. You can only leave group iMessages that have at least three other people
Take care!