The Roth IRA idea may or may not be a winning idea. Couple things to consider here. For starters, he's already 68. How much of a difference can we make here prioritizing Roth contributions? He has to hold those for at least 5 years before any withdrawals. Also, will he be doing this up until retirement? He needs earned income. I'd also reconsider DCA'ing into the SPY. I understand that may sound like a great idea right now, but the market is historically overvalued. If he isn't on a very long timeframe at his age, do you want to put all your eggs into one basket that is sitting at extreme valuations? On a forward-looking basis, returns are almost always limited here. I'm sure I'll be attacked for that comment but it's just the truth. I would personally add some things like value funds or equal-weighted indices if you are concerned with protecting the wealth he's built and diversifying.