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All answers having "Obstacle" as clue:

3 Character Answers:

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BAR

BAY

BYE

LET

RUB



4 Character Answers:

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SNAG

STOP



5 Character Answers:

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FRAIL

HITCH



6 Character Answers:

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HURDLE

LANCET

STYMIE



7 Character Answers:

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BARRIER



8 Character Answers:

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ASSEMBLE



9 Character Answers:

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HINDRANCE

IMPEDANCE

RESILIENT



10 Character Answers:

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IMPEDIMENT

STUMBLINGB



14 Character Answers:

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STUMBLINGBLOCK