I made a multi image selector field control for you. Here's the general idea:
This is a field control that inherits from TextField. In the template of the field I have added a few controls, one of which is a Grid that uses a GridBinder to get images through our Content service and bind them to the Grid. In the textbox of the field, I am keeping an array of the GUIDs of all images that are added. What I change when deleting/adding a new image is just the FilterExpression of the GridBinder which is used to filter the images that are returned by the content service. It's a bit complicated, so if you have any questions, feel free to ask (or if you find any bugs).
In order to install the control, add a reference to the assembly of the control, then add a VirtualPath, using the VirtualPathProvider so that the embedded templates/scripts can be loaded from the control's assembly. The Virtual Path that should be registered is ~/Ctrls/* (check the screenshot to see how to add it):
Next, go to CustomFields (for News for example) and add a field of type LongText, specify a title that you wish and add a CustomWidget for displaying data of type:
Hope the control suits your needs.
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