To confirm, the makemigrations did not throw an error but migrate does.
If I had to try and debug this, my primary objective would be to try and isolate where the error is occurring (which component).
The first thing I’d do is try it with CPython 3.4 and Django 2.0 to try and determine if the issue is IronPython or Django.
I might also change database engines being used in the IronPython version to see if there’s some sort of driver incompatibility involved. (I’d be concerned about the drivers working for something like psycopg2.)