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For the second one, it shouldn't take 20 min, though it is quite a walk. You should probably wait until you have Red Death unlocked before trying that one just because of how fast he is.
For the second one, you actually did it wrong if you were able to walk for 20 minutes. As per the wiki: "The player must enter Green Acres with Hyper Mode and Hurry Mode enabled. After heading south 18 tilesets and west 18 tilesets, the area's appearance will change drastically." Hurry mode doubles the time speed, so it would end at 15 minutes. This one also requires the Sign, so if that was the issue with the first one, this wouldn't have worked regardless.
For the third one, it just requires you to 'heal' a certain amount in that stage using the Dusting. Perhaps you didn't walk around enough to hit the plants enough until the third time. None of the challenges are random, other than potentially getting the weapons required.