Keeping users in context with modal window or shifting user to another page

I'm working on a UI that consists of a list of items that I have received. From this list I can click on the 'pick list' which is an enhanced cart/wishlist in this application. I currently have it designed as a modal window to keep the user in context of the current items they have received and the task they are working on. Within this modal window they need the ability to add a photo and or a description. The issue of this is there is a lot of content to have in this modal window so I believe it would need yet another modal window on top of the already open modal window. Looking for any suggestions or best practices around this.

I found an example of this on Facebook. When you update profile photo, then try to add a photo it brings up two modal windows and keeps you in the context of both the original page you were on as well as the update profile modal window.

So is it better to bring the user to another dedicated page and away from the context or use multiple modal windows to maintain context?