Okay, you're not going to believe this, but after a few more hours of fiddling around with these iPods I've happened across what could only be described as a miracle. I had basically given up and decided to install rockbox on both devices, and just sync music that way. after I installed the bootloader on the 7th gen, I plugged in the 5th gen and decided to mess with the properties a bit. As I right-clicked on the device, I noticed a new menu option had popped up, "Open as a Portable Device". I clicked it, and opened Musicbee. I noticed the iPod 5th gen was now being read as an iPod! In pure disbelief, I ejected the device and plugged it back in. Still an iPod!
I 'm going to be honest, at this point I really don't know if that made a difference, if the universe decided to give me a win, or what. The 7th gen was still not being recognized as an iPod(up to this point) so I unplugged that one and started loading some playlists onto the 5th gen. I've mentioned before, but the 5th gen has a better dac, and more storage, so I loaded a large majority of my lossless playlists onto the device, and used the playlist converter that someone here on the forums had made to get the playlists to be recognized in rockbox. Something I think is important to mention, The iPod was booted into the normal apple os. When I unplugged it, all my music, playlists, etc. were there, and when I booted into rockbox, the same thing. all my music, playlists, etc. were there as well. I use Rockscrobbler, which imports the logs that rockbox makes when playing music, so all my playcounts and such get transferred.
Now, moving onto the more exciting part. To my knowledge, he biggest downfall of using iPods on windows is the fact that the libraries will be identical when syncing with Musicbee. another "miracle" happened with the 7th gen ipod, when I plugged up the device into my PC again, i went back to Musicbee, and noticed it was being read as an iPod as well! with both devices connected, they show up in iTunes as separate iPods with the correct names, and are case-sensitive as well. Last thing I decided to take a look at was iTunes. I opened it up to change the name of the iPod 7th gen, and noticed that for some reason, the "enable disk use" option was still off this time. Going back to Musicbee, I Decided to try the on the fly conversion for the 7th gen, since it has less storage.
it worked perfectly! I don't know if any of this information will help you; what this all has shown be is that these devices are so particular it makes it difficult to pinpoint what the exact solutions are to certain problems. But you already knew that. Thank you again(so much) for helping me over the last few weeks. I couldn't have gotten this working without you. If you have any questions, or want me to be more specific about this mountain of text, lemme know. https://imgur.com/a/iyblRKR
Here are some pictures to show i'm not crazy.