Advice on how to dissuade someone from purchasing a property?

[Benson Chi]

BP,

A person I will name, Bob, once lived in Hawaii and wants to purchase a Hawaiian property for the sole purpose of having a vacation home for his family and extended family. In most situations, this is a thoughtful idea, but in the long run, is a huge burden for everyone involved. Unwavering from this idea and ignoring the good advice from his family, Bob has comps from Hawaii at his office. To complicate the matter more, Bob is no stranger to real estate investing, having over 30 successful years in the business. Due to the progression of Bob's inquiries, this has become serious enough topic to warrant a BP post.

List of attempted reasons not to invest:

• Bob already has extended family in Hawaii!
• No cash flow
• It's so important to repeat again: zero to no chance of generating cash flow
• Expenses in the form of maintenance, insurance, property taxes, etc...
• Bob, you're nuts

Any other advice would help. The last resort is to ping a BP real estate agent from Hawaii to pull comps for me :(