20th Hemingway Regata sails in Havana

The video provides a brief message of encouragement, wishing the audience good luck.

What does the phrase 'Good luck with that' imply about the speaker's attitude?

In what contexts might someone say 'Good luck with that'?

How can the phrase 'Good luck with that' be interpreted in a conversation?

What feelings or emotions might be associated with saying 'Good luck with that'?

Can 'Good luck with that' be considered supportive or sarcastic? Explain your reasoning.