Hi anon, I'm going to make an inference here and assume that you won't have any issues with regards to an emergency fund or insurance coverage. With that said, let's look at the considerations for your question. $24K/yr dividends at 5% can be achieved through a combination of high yield bond funds, balanced funds, REITs and equities. You will want to analyze which holdings can give you sustainable and consistent payouts, have strong fundamentals and good management. This will be doable for REITs and equities, less so for funds, but still not impossible. Once that's done, have an idea of how you want to allocate your portfolio in terms of position sizing. You should not have too much concentrated in a single stock or UT, but not so many holdings that managing and monitoring become difficult. Once you have an idea of which holdings you want, you can then look at your entry prices. It is better to wait for a good price rather than jump the gun and deploy all $480K at one go. It might take a few years to deploy your funds, but there's no harm in treading with caution. Once you have achieved $24k/yr dividends, it's a matter of monitoring and adding on when opportunities allow or taking profit if your holding has run up. Over time, saving part of your dividends and re-injecting into the portfolio will allow you to increase your payouts. Just note that by going with a fully variable investment, you are exposed to market risk, so there will be times that your dividends may be reduced, so in time to come you will want to take your variable payouts and convert them to guaranteed sources of income to increase the reliability of your payouts as you approach retirement.