And finally I'm done!!! Found a couple of bugs in solution logic (lack of extra loop)

The clue was extreme logging/printing when debugging move by move and even shot by shot!

There must be some bug in your solution. I just passed all the Example tests, all Fixed and 98 out of 100 Random tests. Need to find my own bug as well :)

There is no such Roman numeral, no. 1990 is MCMXC.

Can't make heads or tails of what you're saying. What's a cycle?
Note that you sometimes print out the documents, but not always. Maybe you're looking at the wrong document.
In my solution I'm able to re-order the nationality-check and expiration-check and it's passing either way.
regarding what's logical, it doesn't matter what you think makes sense, only what the spec is. in this case, either order is fine.

Your code works for values up to 100. Testing goes up to I think 1 000 000.

( Shouldn't that be range(2,arg) then ?!? [ And even that is highly suboptimal. ] )