Potential answers for "Penny, maybe"

⭐⭐⭐⭐ ANTE
⭐⭐ OLDSAW
⭐⭐ ADAGE
⭐⭐ STAMPS
⭐⭐ ADAGES
⭐⭐ RARECOIN
⭐ PLEADER
⭐ OLEO
⭐ AGE

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Do some course prep   Goes from Tokyo to Kyoto, say   Hard-to-solve problem