Hey Justin,

To answer the question about the avatar priorities, no order combination should cause problems, it's simply where it looks first before moving on to the next. For example if you have Gravatar followed by WP Avatar, it will look for a Gravatar first and if it doesn't find one will move on to look for WP Avatar.

I would suggest looking at the file size of the image to make sure it doesn't exceed that of the limit in place, although by the sound of that and the broken images it could also possibly be a folder read/write permission issue.

Please remember though, this 'Pre-Membership Queries' forum is really for use as the title suggests, not for support but for pre-purchase product questions. Happy to answer any further questions about Simple:Press but for further support please open up a topic in our support forum.