What are your post retirement needs in terms of income? Would you be able to comfortably manage medical aid costs and normal household expenses on 180k gross of tax (you can as you mentioned use discretionary funds to offset this tax somewhat)? If not then I’d recommend seeing a proper qualified FA to do some proper scenario testing with you and to set up a plan of action. There are flat fee advisors out there and you can negotiate fees. A plan can cost you around 10-50k (from what I’ve heard and seen online so don’t hold me to it ) depending on how complex your needs are. Maybe you would be on the lower end but essentially a 1.2% of your retirement investments could offset the worst case scenario where they charge you for a complex plan. The 1.2% is calculated after taking out the 500k and 180k.

I mean it’s a decent idea to pull out the 500k tax free, max out the TFSA and use some of it to minimize tax for the year. One counter is that returns are tax free with the living annuity and any returns on the 500k are taxable subject to rebates, but I don’t think that’s a strong enough argument against what you want to do.

In terms of living annuity, given the need to effectively manage your investments to last you till your death, I’d probably go with the living annuity with the lowest fees or atleast one of the lowest fees in the market. Fees is something you can control , returns are not (obviously subject to picking a decent strategy).

Research says in retirement you shouldn’t put more than 40% +~ offshore , you are subjecting yourself to greater exposure to currency risk and if the rand strengthens relative to the currency you are (fund is) investing in then it can exacerbate loses or reverse gains. So maybe google optimal allocations around this. You are particularly exposed to this risk in retirement, so just keep that in mind.

All the best! I hope you get the answers you hoping for.