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Ya I did all that. Interestingly, I was sent a picture from a non-iPhone (so via MMS) and now all pictures are showing up. Yesterday I was only testing with other iMessage users. Perhaps the non-iPhone user caused the images database/file on the phone to start working again. Strange.
Went from iOS 7.1.2 on iPhone 5 to iOS 8 on iPhone 6 today. Any new pictures that are sent to me in messages do not display and just show "Downloading xxxKB/xxxKB" as a placeholder. See here: http://i.imgur.com/DehPJgR.png
After rebooting the phone those Downloading placeholders just turn into...
Does the carrier update that iTunes prompts you to install (not the 2.2.1 update) mess up any jailbreak on your phone? I heard it was just an update on how iPhone connects to AT&T network, but you never know...