I was scrolling through Reddit recently and came across a post in the r/fatFIRE community that sparked some interesting conversation about cash flow strategies for those who have already achieved financial independence. 

At 39, single, and living off rental income, the user finds their current strategy underperforming and wonders whether it’s time to pivot to a dividend portfolio or a market ETF with a withdrawal plan.

Let’s take a closer look at their situation and potential pathways for optimizing cash flow:

Their Current Situation

Currently, this user has:

• Assets: $2.5M in real estate (3 properties, 11 doors).
• Rental Income: $9,500/month on average.
• Future Plans: A Roth IRA expected to reach $2M+ by their 60s.

Despite their high number of assets, the user is considering selling their real estate and reinvesting the money into an investment portfolio instead. If they adopted a 5% withdrawal strategy, they estimate they could earn $10,400 a month, which is slightly higher than their rental income. 

What Are the Potential Options?

There are several potential options for the poster:

1. Stick with real estate: Potentially, the user could decide to stick with real estate. This provides the potential for long-term appreciation and several tax advantages, like depreciation. However, rental income can be a little volatile, especially when you throw maintenance costs into the mix. 
2. Shift to a dividend portfolio: A dividend portfolio could provide around 3-5% annually, providing a reliable income. Plus, there is less maintenance involved and some potential tax advantages. However, dividends aren’t promised, and yields can change regularly. 
3. Invest in a whole market ETF: The user has mentioned investing in a whole market ETF and then withdrawing money at a rate of 5%. Broad diversification like this reduces risk and provides a simple, low-cost strategy for those who don’t want to monitor individual assets. Withdrawing 5% annually may erode the principal down, though, as this rate is very high. 

Key Factors to Consider

• Tax implications: Selling real estate may trigger significant capital gains taxes. A 1031 exchange could defer taxes but would require reinvesting in other properties.
• Risk tolerance: Real estate offers steady income but comes with operational challenges. Market-based investments provide greater liquidity but expose you to market volatility.
• Lifestyle preferences: Real estate often requires more time and attention, even if you aren’t maintaining the properties yourself. Transitioning to traditional investments can make sense for some who prefer to be more hands-off.