1. The annuity does not seem like a good solution. The embedded fees are high, and I'm not sure that it would even solve your Dad's problem, which is that his expenses are too high relative to his assets.
2. I can address the family dynamics: In my experience, parents tend not to listen to children in these cases. No one likes to hear that they need to cut back on their lifestyle, especially when that message is coming from a child. I have experienced this in my own family and seen it with clients. It's just an unfortunate fact. In general, parents will only start listening when things have reach crisis-level, but of course you want to avoid that. An alternative would be to bring in a third party to help you communicate with your father in a way that is both empathetic but also quantitative/logical. That could be an accountant or a lawyer or a financial planner (not an annuity salesman, but a real planner), or even a social worker. It needs to be someone well versed in the numbers and also well versed in family dynamics. It needs to be someone who won't just point at numbers on paper but who will also understand the underlying reasons why he won't sell the big house or leave the country club, for example.
Just today I played that role for a client, and I can tell you a little bit about what it looked like. I spent two hours in a house just like yours -- a divorced parent around the same age together with a concerned child. Going into the meeting, the child was really nervous, not knowing how the parent would react. But, it really seemed to help to have an independent person in the room providing the child with back-up, confirming what the child had been telling the parent. Importantly, I (and the child) didn't dictate any solutions; instead, we just offered alternatives: work part-time, trim expenses (no need to live like a pauper, just cut something), put the vacation house on Airbnb, put idle cash into short-term bonds (not bond funds, but individual bonds, and hold to maturity). I had lots of numbers on paper, but I also spent a lot of time just talking with the parent, exploring solutions and generally being supportive of the very difficult situation.
Another suggestion: try to meet with your siblings and see if you can get them on the same page. You definitely don't want to gang up on your Dad, but at the same time, if you are all on the same page, then you can deliver a consistent message, and that will definitely help. In my experience, when each child has a different opinion (e.g., hold the house but quit the club or vice versa), and is communicating it separately to the parent, then the parent really won't make any progress.
You shouldn't expect to solve this overnight, but with a combined effort, and over time, I am confident you'll get there. Good luck.
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