I also felt that the quiz was lacking in realism. I can understand why you used computer-generated images, but would suggest that you could have gotten more realistic ones. For example I was uncertain whether the first picture was flying over sea or flying over forest, at first. Some of the flight simulator scenery packs would make for much better images.
Trees in Canada are much taller than trees in the UK. I can't comment on trees in New-Zealand or on FS, but I have been caught out misjudging distances whilst walking in Canada. This will certainly have affected my guesstimates of altitude and visibility.
I might not choose to fly in some of the weather you've shown, but if you're truly 'nearly at' your destination airfield, the question isn't whether it's safe to continue but whether it's safer to land than to turn back. To be honest, I don't particularly enjoy flying along just under cloudbase but I wouldn't have felt particularly threatened by any of the pictures you provided. I would have worried about embedded cumulo-nimbus in some of them.
All of your terrain was basically unlandable and reasonably flat, so I was less concerned about cloudbase than I normally would be. Given an engine failure the chances are you're ending up in the trees whatever altitude you're flying at, though at 3000 feet you may have just that bit longer to work out how to restart the engine. The chances of being caught between rising ground and cloudbase weren't particularly high.
I found your assessment-of-cloudbase questions quite interesting. The decisionmaking questions were harder to answer, because ordinarily you have so many more factors to take into consideration than a simple picture can give.