So I got half-way with this. At the very least, I got the files copied and DSK2File to work. What I did was:
Create a ProDOS .img Disk Copy file on one of my Macs, and transferred it to my MacBook Pro. Using CiderPress, I copied each file from the .dsk image to the .img
image. I then copied the .img back to my other Mac and made a real 800k floppy from it. This preserved the file types and I was able to open DSK2File on the IIe side.
The issue I now have is that using DSK2File, I attempted to make a disk from the image I have (Oregon Trail, if you must know). Once it was done writing the disk, it appears that it somehow screwed up because the disk was unable to boot, and it appears to be empty. Not sure what went wrong, but I’ll try again tonight. I know the image is good because I used it under GSpot without issue.