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Notes -
I have a general rule that I do not make big changes regarding financial situations or anything else that are predicated on assumptions about future political or legal actions.
For example, there is a fairly common strategy of converting IRAs and 401ks which are pretax (meaning that you have not yet paid taxes on them but will need to do so upon withdrawal) into Roth IRAs and 401ks (which will be tax-free upon withdrawal). To do this you need to pay taxes today to attempt to save taxes in the future; as such it is basically a bet on your tax rate today vs. at retirement. However the hidden assumption is that Roth vehicles will never be taxed, and I put the odds of that at much lower than 100%. We're going to need to get that UBI money from someone.
That being said I didn't think I'd ever sniff Social Security and I now have <20 years max left (pending changes to retirement age). But I have found that eking out small +EV in life tends to be dwarfed by variance. At the poker table sure, but not when dealing with the vicissitudes of fate.
I've always felt similar about Australia's Superannuation system. There's definitely ways of deriving a tax advantage, but as a 29 year old now I'm not super confident in the withdrawal ages and sanctity of the product for the next half-century.
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