Yes and no. It’s a bit hard to see I know because there is so much going on as well as there are some special cases missing on that image.
Here is a better example:
Labels try to be over the item they concern (1)
If there are items that are too close together, labels start moving to not overlap one another. (2)
This seems to work even with differently sized labels (3)
Of course my end result does not be this one to one.
I’m just wondering if trying to create a system like this with Blueprints is something worth pursuing 
I’ll try playing around with approaching the generation of the layout in a different way. Maybe generating it while adding the labels to the container and making sure they already lay themselves out correctly during generation might give me some improvements. Maybe I can get rid of a couple of loops that iterate through 40+ objects. That would help I guess ^^