Is there a way to assign different mapped drives to the same drive letter?

"The only way I can see doing it is to change the drive letter for one of network drives" is correct unless you're using some clever software.
In essence two mapped resources to the same drive letter is chaos and cannot be represented on a user PC.

No... One mapping at a time... How would the system know you wanted X: mapped to \\server1\share  or X: mapped to \\server2\share?

The second mapping disconnects the first, or you get an error..

I don't know if it makes a difference but I'm pushing these out via GPO. I was wondering if naming them differently would work, but they would just have two H: drives going to different locations? I can't remember ever seeing this though.

Again... No... One instance of each drive letter is allowed... Just one.... Only one...  Per PC....

Now PC1 can have H: pointing in a completely different place than PC2, But each computer only gets one mapping to each UNUSED letter... If the letter is already grabbed by system hardware like a DVD drive or such, it will not map reliably...

Yes that is true, I had forgot about that. Consider this case closed.

Seems to me you are saying you want F: mapped to FolderA and FolderB at the same time.  Well, you can't do exactly that but, you could create a FolderC, map F: to folderC, then move FolderA and FolderB to Folder C so that both would be available under F:
 
You should be able to do this without actually copying/moving the folders to FolderC... use symbolic links.

https://www.howtogeek.com/howto/16226/complete-guide-to-symbolic-links-symlinks-on-windows-or-linux/

You can play around with junctions. Perhaps one "master drive" with network junction folders?

mklink /D S:\MapDrive1\\someserver\someshare1\foldername1
mklink /D S:\MapDrive2 \\someserver\someshare2\foldername2

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i still wonder WHY you would like to do that?
Patrick, come back and tell us; you can also close this Q then

This can be closed. It was decided not to pursue this.

You can close by choosing the best answer(s).

Patrick - why don't you answer my questio " i still wonder WHY you would like to do that?"

I should have objected to this one... I gave pretty much the same answer first...

Me, too... not the first answer, but the first answer as to how he could get both folders associated with a mapped folder by using links.