It seems like you're finally at the point where Maddie's stuff is mostly out (except for the drawers under the bed that could possibly be brought to her new room to be sorted through) so you'll be able to make even quicker decisions and progress and get to the organization part next time.
I wonder if the white drawer and shelf units would fit, heightwise, on the large shelves? The space this move would create in the corner would be perfect for the cart, away from the closet door.
I watch a lot of decluttering videos (I’m retired). You have been doing the decluttering of your house for a little while now and we are starting to see some progress. I hope you get your office the way you want it so you can use it for crafting finally. I have noticed that you have a hard time letting go of things that are memories of Maddie’s childhood years. Especially the American Doll stuff and the Disney things. If she doesn’t want them, and you don’t have anyone you want to give them too, then can you donate them to a charity?? Maybe into her memory bin?
For goodness sake there’s only so much grace to give. Jen has been at this for years, it’s time to get tough if she is ever going to reach her goals. I think she is a lovely lady but boy is she indecisive.