Hierarchy of Risk in Terms of Different Accounts such as Roth, IRA, HSA and Taxable
I have traditional IRAs, Roth IRAs, HSAs and Taxable Brokerage Accounts. I currently have a bunch of cash to allocate as I have moved things around recently. I am over 59 so everything is accessible and I do not plan to retire for at least another 10 years assuming nothing changes. Let’s assume I have enough for one year in a HYSA so that is not part of this discussion, I am only thinking of investable assets.
Some of my investments are riskier than others but nothing crazy (CEFs, dividend paying stocks, individual growth stocks, large sector ETFs such as VOO and QQQ). I generally do not trade options although I have in the past. Not concerned whether appreciation comes in terms of growth or dividends). Not overly concerned about taxes on brokerage accounts.
In thinking about it, I believe that my riskiest investments should be in my traditional IRA since that is money I have not paid tax on. Then my HSA for the same reason although withdrawals will be tax free (I have lots of old medical bills), then my taxable brokerage because although I paid tax on the investment, I have not paid tax on the gains and finally my safest investments (assuming that even exists) in my Roth where all withdrawals are tax free and for my descendants as well. I do wonder if I should put my HSA in safer investments than my taxable brokerage. I am a glass half empty person so I realize I am looking at it from a loss perspective as opposed to a gain perspective.
Thoughts? Am I looking at this correctly?