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I'm not sure I agree, since there's words like "bookkeeper" that work fine—people just add a stop in front of the k sound and don't really think about it.

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I never hear people say "bookkeeper" in everyday language. It's usually shortened to "bookie"

bookie (maybe this is UK) is usually short for book maker, not bookkeeper.

Ah yeah you are right, TIL they are different

Same in Australia!

(US) A bookkeeper keeps formal records of finances. A bookie manages bets in gambling.

roommate. school loan.

Those do not have hard stops in the middle.

Roommate does, people just don’t use it.

Then it doesn’t.

True. But in both cases, you can pronounce the first vowel open or you can close it.

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