ParseJSON doesn’t return JSONItems at all.
Kind of sounds like you might be mixing the old global framework with the Xojo framework.
I like the Old framework better with JSONitem. Works much like everything else in the global framework.
The new framework uses Auto and you have use Introspection to tell if it’s an array (of Xojo.Core.Dictionary’s) or a singular item (Xojo.Core.Dictionary). Not nearly as user friendly IMO, though it has its uses.
If anyone knows a better way / method for me to navigate this I am 110% open to any links or pseudo code. 
Take a look at my JSONItem_MTC project here:
https://github.com/ktekinay/JSONItem_MTC
In includes ParseJSON_MTC and GenerateJSON_MTC functions that work like the Xojo framework calls, but entirely with the classic framework.
Thanks Kem! Will do.