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PD: of course, you don't have to do the 20 barrel rolls "in a row" meaning one after another, you can take all the time you want, also between several regions :)
Just spread them out through each region, and nail as many between regions as you can get.
Later they ask you to do X barrel rolls in one region. That sucks.
A lot of these 'challenges' are rather ridiculous, with many of them made easier by stuff that is unlocked later in the levelling. The only move right/left through multiple regions is nigh impossible without jump, and made infinitely easier via shield.