Possible Clues:

• Easy and unobstructed progress
• I may get in maps not fit for easy ride
• No problem with Jumbo announcing one is going overseas
• No problem in 23 down going overseas
• Simple aircraft's weak by the sound of it
• Progress without obstruction from one disrupting schemes in a bad way
• Straightforward progress shown by student beset by troubles, suffering?
• Simple Plan covering single, one by Rod Stewart
• Easy progress, but suffering on grasslands
• Intends to circle island in poor health, getting uninterrupted progress