Thanks for getting back to me on this :D
(1) I was attempting to use POE but may try an AC adapter if i can find one lying around. Also, I think when Dan and I tried flashing it last night at the meet-up it was over POE and he was able to get the script to at least start transferring, but he was also using a different usb adapter. My next goal is to find a different usb adapter and try that out.
(2) The usb adapter is a manual one so it's possible something was off with my configuration even though I checked it a bunch of times (though it was pretty late in the evening lol). Shoutout to Max: did you have problems with this adapter when you were using it?
(3) That is a reallllly good question and I didn't even think of that possibility! I'll dig through the meraki docs to see if any mention is made regarding that.