I've noticed something strange - if a user submits something for approval, and I log in as a moderator to approve it;

1) If I view the item and submit it, it is approved BUT the user does not get an approval notice (not ideal)

2) If I just click on Approve (or Reject) - then they get a notice.

But often I want to modify a few things and then approve - but it's critical that they are notified... so I have to Approve it with the button and then go and edit it. Is this by design?

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The reject function should do the following:

1. open a textbox where you can enter a rejection reason
2. send an email to the uploader which includes the rejection reason
3. delete the file and/or image
4. remove the record from the repository tables
4. rebind the moderation list so that the item you just rejected is no longer displayed and you can continue to moderate other items

so, if that's not the behavior you are seeing, then something is wrong. If an exception is being thrown at some point, it's possible that it's not being caught and the exception is being lost, resulting in an incomplete process.

Looking at the code, the process of creating and sending the email is not being done within a Try-Catch block ( BAD programmer!!!! ) ... :)  so if the process of sending the email fails .. which in your case looks like it is .. then the file will not be deleted or removed from the list of items to be moderated.

There should be some errors logged if the SendMail() function is throwing an exception. Check your logs and see if there are any entries that might explain why the rejection emails are not being sent.