GMAT Sentence Correction (SC) | Need help deciding/todecide whether to use gerunds or infinitives ?

One example would be my question itself.

When I say, Baby I don't want your dollar bills to have fun tonight. Do I not want dollar bills-?personified- to have fun? or the other (?obvious) meaning ?
Had it been , baby I don't want your dollar bills having fun tonight. Would that make the difference?

EDIT:
You need to continue to study? (not studying)
I need to practice listening ? (not to listen)

Can someone break it down please ?

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