One Fetch Quest in Donald's Dreamland has a shop owner reject your pajama delivery because she doesn't want to own blue pajamas. This may have just been meant as a joke (the shirt she's wearing is blue!), but it's actually a semi-valid complaint. Looking at the color blue has been scientifically proven to make it harder to fall asleep.
Why does Lil' Oldman give you such difficult and grinding Toontasks? Several reasons, actually. First, Lil' Oldman is Flippy's mentor, and Flippy is the mayor of Toontown, making him a high-value target for the Cogs. If any Cogs break into Toontown Central, Flippy has to be prepared for anything, from defending his office to saving other important buildings from being occupied by Cogs. Second, Lil' Oldman is preparing the Toon for Donald's Dreamland, where the tasks get even harder. And third, Rewritten reveals that Lil' Oldman is an actual wizard—he specifically refers to your Toon as an "apprentice" and wizards would put their apprentices through extremely tough tests to ensure they could face any danger.