Upload multiple images in a custom metabox

That’s pretty advanced and it doesn’t sound like you are all that comfortable with WP yet, no offense. You can definitely do this with WP Alchemy (I have and do), but you really have to get down and dirty with some Javascript to 1. launch the media uploader and 2. to hijack the send to editor function.

some good reads:
http://austinpassy.com/snippets/wordpress/creating-custom-metaboxes-and-the-built-in-uploader/
http://www.krishnakantsharma.com/2012/01/image-uploads-on-wordpress-admin-screens-using-jquery-and-new-plupload/

As far as alternatives: you might want to try the the Metabox class by Rilwis.
http://www.deluxeblogtips.com/meta-box

or Advanced Custom Fields
http://www.advancedcustomfields.com/

Both are much less DIY than Alchemy. I’m pretty sure the one by Rilwis even has the plupload drag and drop uploading and a simple way to turn on repeating fields.

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