I have attempted to answer it twice and failed
I'm guessing these were "into the headwind" and "with the tailwind"? What other options are left? The answer is a few posts above.
Bloody dangerous and illegal
Dangerous, yes! Illegal? No. VMC (class G) below 3000ft means you simply need to be clear of cloud. I guess it depends how high the cloud tops were in the instructor's question...and that they are in non-controlled airspace and not a GAAP, I mean, Class D airspace.
To be honest though, the instructor is just pulling his own wang indulging in his self-importance by keeping the student guessing. Bloody three-bared rock star.