Possible Clues:

• Like some expenses
• Like some expenses, and how the answers to the starred clues are made?
• Like medical expenses you pay for yourself
• Having lost money fallen through hole in trousers?
• Certain expenses
• Made poorer by a transaction
• Having suffered loss, produce handkerchief here?
• Unbudgeted (of expenses)
• Requiring a cash outlay
• Paid in cash coming from Pip's friend