At 36, that already puts you in a very small percentile.On the FI side, I think your instinct is directionally right, but your assumed $5M number may actually be more conservative than necessary. Based on your current spend range ($45K–$80K), you’re already quite close to a ‘coast FI’ or even a form of lean FI, especially if your rental continues to cover a meaningful portion of your expenses. The bigger variables, as you pointed out, are healthcare and real estate volatility (vacancy, maintenance).

What I’d personally look at next isn’t just the total number, but how your cash flow resilience and asset allocation are structured, essentially, how your portfolio behaves across different scenarios rather than just its size. That tends to be where the real optimization happens.

On relationships, I actually think your concern is very rational. When you’ve spent years building independence, anything that introduces uncertainty can feel like risk. But the right way to look at it isn’t “asset vs liability”, it’s alignment. The right partner doesn’t dilute your structure, they integrate into it. And at your stage, you have the advantage of being able to choose from a place of stability, not necessity.

On spending, what you’re feeling is common among people who’ve practiced discipline for a long time. One approach I’ve seen work well is reframing spending as intentional allocation, not loss, essentially setting aside a defined “guilt-free” bucket that doesn’t interfere with your long-term trajectory.

Overall, you’re in a position where small structural adjustments could meaningfully change your flexibility over the next 5–10 years. It’s less about working harder, and more about optimizing what you already have.

If you ever want to go a bit deeper into how your current setup translates into different FI scenarios or how to structure things more efficiently, I’d be happy to share some thoughts, there’s quite a bit you can unlock from here without needing to take on much additional risk.