See answer to similar question here:
http://stackoverflow.com/questions/16039429/episerver-7-mvc-linkitemcollection-add-images-to-linkitem-collection

Thanks, I have seen that but dont like the idea to implement it as blocks. For webeditors, the user experience of creating blocks for that task will not be as smooth as it would have been to just use a simple linkItemCollection...

For images you can create a Contentarea that only allow images, and then have a displaytemplate for rendering. Editors can then drop images into the contentarea, and skip the step creating blocks

[AllowedTypes(new[] {typeof (ImageData)})]
[UIHint("ImageGallery")]
public virtual ContentArea ImagesContentArea { get; set; }

May be you can get some ideas from this old thread where Anders extended the linkitemcollection property to use visitorgroups.

http://world.episerver.com/blogs/Anders-Hattestad/Dates/2011/6/How-to-make-Property-LinkCollection-use-Visitor-Groups/

Thanks Tahir, I have seen that, it was easier before when the Admin interface wasnt built with Dojo. I dont think that will work in an Epi8 environment..

I agree that Dojo is close to witchcraft. ;) However, there is a lot you can do with custom properties without touching dojo. I recommend reading this excellent post by Allan Thræn:
http://world.episerver.com/blogs/Allan-Thran/Dates/2014/6/Strategies-for-Custom-Properties-in-75/

LinkItemCollection is a very useful property type in EPiServer. However, quite often you need to transform, convert or in some ways prepare a LinkItemCollection before you can use it the way you want to.

Have you considered Property List. Gives the content authors more control in a single view than creating a block for each item.