that'sThat's pretty advanced and it doesn't sound like you are all that comfortable with WP yet, no offense. you You can definitely do this with alchemyWP Alchemy (iI have and do), but you really have to get down and dirty with some javascriptJavascript 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/
asAs far as alternatives: you might want to try the the Metabox class by Rilwis.
http://www.deluxeblogtips.com/meta-box
or advanced custom fieldsAdvanced Custom Fields http://www.advancedcustomfields.com/
bothBoth are much less DIY than alchemyAlchemy. pretty I'm pretty sure the one myby Rilwis even has the plupload drag and drop uploading and a simple way to turn on repeating fields.