I have had the same issue, and also occasionally unable to send photos via MMS. This is the first time I've been unhappy about something with the upgraded software for my iPhone.
I can't mail any photos off my phone at any size. I select a photo, I select to e-mail it, and I select the size. No matter what size I pick, it then time out and fails to create the message.
Same problem. Go thought the same 'email photo process;' select a photo or 2 from camera roll, select email photo, see the photos in the email, type my email address, hit send, select size (small,medium,large,original), and nothing happens, no woosh sound...nothing...
Same problem here iPhone 4 - camera takes photo, hit email. write msg, nothing.. I can go to my email outbox and there it is - waiting to send manually.
Is any progress or solution happening on this issue?
SOLVED: I was using the Exchange setup to sync mail, calendar, contacts with my gmail acct. When I created a standard gMail setup on the phone and chose that as my email - the photo sending from the camera started working again. So I turned off mail in the exchange setup so it only syncs contacts and calendars now and the regular gmail setup syncs mail and notes. Not sure if thats the right way to dod that - but it seems to work.
The photos do send if you set up a regular gmail account, but I think there are some benefits to using the exchange for gmail. There should be a fix for sending photos while still using the exchange account ...right?
The emails getting stuck in the outbox when emailing from the camera roll directly seems to be a bug in iOS 4.0 when you have your Gmail account set up for IMAP and also the same Gmail account set up under Exchange Sync. I had my Gmail account turned on for Exchange sync, but I also had my old IMAP Gmail account, albeit inactive (just to save it in case I needed it as a backup), but still showing in the list of email accounts.
The fix? Delete the IMAP Gmail account from the list, and try to re-send a new photo from camera roll. It will no longer get stuck in the outbox! Seems like iOS 4.0.1 does not play well with having the same email account set up multiple ways (in this case, IMAP and Exchange).