My answers are for American English (of course).
First, there’s no “seventeen”. We can say “a hundred seventy-eight dollars” for $178.00. We can say “a dollar seventy-eight (cents)” for $1.78. In this context, we can say “one” or “a” with no difference in meaning, although we would usually say “one” if we wanted to emphasize that. Also, note that we can refer to “dollars” as “bucks” in everyday speech.
In casual speech, we can say “one seventy-eight” for both prices. If the meaning is not obvious from context, you’ve got bigger fish to fry.
Question 2:
It’s true that ”the babies' diaper" and" the baby's diaper" are both pronounced the same, however it will be obvious from the context. Also, if there are multiple babies, there will normally be multiple diapers.