I'd love a good answer to this...
currently I have been using either...
a) the dataobject either has a whole bunch of $has_one 'Image' (Image1, Image2,...) and then I use SimpleImageField on the public facing site and the default field type in the ModelAdmin
b) I have a $has_one 'Folder' in the assets where the admin then uploads all relevant media into that part
c) (which I do not do anymore) is $has_many to a small data object that contains only a $has_one 'Image' this means you can add/remove as many as you'd like on a thrid tab but the amount of clicks is obscene so it was dropped for one of the above
...I know there is the DOM with SWFUpload and Uncle Cheese should be rightly proud of this and explain how it can help...
...but for those purists of use that want to use the core ModelAdmin...
...I'd love a good answer to this...
...please :)
Barry