@JJ-Fullmer Well this is an interesting one as we obviously never had anyone wanting to resize this kind of partition layout yet.
As we can see from your posts the old disk is a lot larger than the new one:
Disk /dev/sda: 465.8 GiB, 500107862016 bytes, 976773168 sectors
vs.
Disk /dev/sda: 111.8 GiB, 120034123776 bytes, 234441648 sectors
While this does not have to be a problem per se it is causing an issue in your case because sda3 and sda4 start at a position way beyond the SSD capacity. If my understanding of the magic resize algorithm is correct we don’t move any start sectors of any of the partitions as this might cause an issue. We keep all the start sectors and only shrink/expand the partitions. This is usually fine because most installations have the big system partition last and therefore this is being shrunk/expanded.
A couple of times Tom and I have discussed rewriting that magic resize algorithm and improving it. Your case would definitely be on the list for improvements. But on the other hand we are a bit worried about making things worse because we would need to do assumptions on which partition’s start sector can be moved and which can’t (windows boot partitions are very picky with being moved!). A lot of things can go wrong if we need to do those kind of guess work.