Disclaimer: As far as I know, I'm not going to die soon. I'm asking this question in case that changes someday.
So I was just thinking about this and thought it might be a good idea to leave your family some money while fucking over the bank on your way out. The creditors would go after your worthless estate only to find the recently purchased assets are missing, but you're already dead and can't be charged with fraud. And if you do some decent opsec, they can't implicate your family either.
I assume without laundering the money, your family would not be able to use it on anything big. And your available credit wouldn't be enough to make a massive quality of life improvement for your loved ones. But even if they only spend it on groceries and hobbies for a few years, it would make a nice goodbye gift.
Am I missing anything that makes this a horrible or unacceptably risky idea?
This is a great concern and I need to elaborate some points.
"diversify", as a key element to the strategy, includes where you buy things, what types of things you buy, and who receives things. If you can rotate between 10-100 beneficiaries, it'll be harder to audit than 2-5 beneficiaries.
Avoid luxury things. Lifestyle audits happen when you're driving a lamborgini but you're a junior tech or work cashier at McDonalds. In fact, avoid gifting larger or numerous things to any specific person who acts flashy. Lifestyle audits are usually somebody thinks you're stealing from your company, or you're doing your taxes wrong and receiving large assests that are heavily documented and regulated (cars, real estate, checks).
Lifestyle audits aren't likely to happen unless you're really loading it all up on a small number of people and they're all trying to dress up and show off like instagram models/influencers while poor.
Keep as many gifts practical, utilitarian, or ordinary as possible. Don't be gifting things that are >$1000 if they must be reported to any random agency or they're not a normal house-hold item the beneficiary claim they threw away the receipt for. Don't buy things only good for peacocking, don't buy things for people who regularly peacock.
IDK about vacations, I'd avoid it or keep it really simple and small.
Grandparents gifting large numbers of small undocumented things is very normal.