Progress on this is currently halted due to RDF not conserving the order of LicenseConjunction/Disjunctions.
General comparers like jd used here are not able to see MIT and GPL-2.0 and GPL-2.0 and MIT as equal.
Thus, we need a custom SPDX comparison. Maybe the java tools CompareDocs once this issue is solved.

I don't know if this helps - but here's a pointer to how the Java library handles this issue:

https://github.com/spdx/Spdx-Java-Library/blob/da021dffa3c2376f2aa2654863fb000be2aa7d2a/src/main/java/org/spdx/library/model/license/DisjunctiveLicenseSet.java#L106

We basically override the equals and hashcode methods to "flatten" the set and do a compare. Equals is overridden in most, if not all, of the license related classes.

MIT and GPL-2.0 and GPL-2.0 and MIT as equal.

"fun" fact: I am not sure if the legal thread agrees that these two expressions are equal. As far as I remember, in some discussions it was stated that they should not be treated as interchangeable but instead if Legal decides to say "MIT and GPL-2.0" this specific expression needs to be preserved.

After discussing this again, a quick fix for the problem is to simply exclude AND and OR license expressions from the test file. With this, the core of the test is still intact and we don't lose very much test coverage.