What is your opinion on transferring funds from one’s Ordinary Account to their Special Account? Are there more advantages than disadvantages to this approach, and what are they?

The advantage would simply be the accelerated impact of compounding in SA. I sometimes wish I had done that earlier in my 20s, as 10 years does make a difference. (In my case, I would probably have around 50K more in SA by now if I transferred every cent during the first 2 years of my work) It will help you get to FRS faster, and you will worry less about the FRS going up year on year. If your sum in SA is sufficient, the interest alone will negate the yearly increase in SA, and help build your retirement safety net.

Having said that, it is a one-way thing, so you will have lesser CPF OA funds available for housing, education and the like. You will have to weigh your options based on where you are in life now.

However, I do advocate leaving at least $20K in OA as that earns 3.5% interest, which is not too far off from 4%, but still gives you the flexibility to utilize for housing payments, etc.

At the very least, transfer OA to SA till it reaches 40k! 25 years down the road, you’ll get more than 100k for that 40k! That itself is a big plus plus plus point!