Conversation so far:
When did Waugh have issues in the Caribbean?
Mark Taylor retired at the end of the 1998-99 season and Waugh replaced him as Test captain, beginning with a tour of the Caribbean.
What team did he play for?
Australia.
How did the Kiwi's play first?
CANNOTANSWER.

Question: How did Waugh struggle?
Self-contained rewrite: How did Steve Waugh struggle in the Caribbean?