When perusing the Google for some answers, I came across the following little gem c/o Ryan Marganti. In his words:
“When managing a multi-user WordPress setup, any post by a user with the Contributor class will be held for editing/moderation [...]. However, the downside to the Contributor class is that users with this role are not able to upload images for use in their posts. Luckily, the solution is simple.”
The solution:
All you have to do is plug the following into the functions.php of your current theme.
if ( current_user_can('contributor') && !current_user_can('upload_files') )
add_action('admin_init', 'allow_contributor_uploads');
function allow_contributor_uploads() {
$contributor = get_role('contributor');
$contributor->add_cap('upload_files');
}
I just tested it, and it works like a charm. This opens up some exciting doors for a new potential project, thanks Ryan!
When I joke that I’m over Twitter, what I really mean is that my initial passion/overusage has dwindled since I first started using it back in 2007 with various pseudonyms. Back then I felt like an early adopter (sure, Twitter was launched in 2006, but c’mon, virtually nobody used it for the first year). Now every local mom and pop is trying to encourage you to follow them on Twitter, as if they had any idea why they’d want you to do that (for those interested, 
I looked all over for this code and it took me forever to figure it out, so I thought I’d post it here for anyone else that happens upon it (let me know with a comment!)
