There's two things I find worth considering as maybe-wrong: 1) non-public investment opportunities in combination with tax-free status 2) no sanity threshold

There's two things I find worth considering as maybe-wrong: 1) non-public investment opportunities in combination with tax-free status 2) no sanity threshold to collect some taxes after your Roth balance becomes large enough 1 is maybe a violation of the spirit of what a Roth was designed to be used for. You should be able to invest (cash only would be dumb), but you shouldn't get tax free returns for every kind of investment you make. Public shares might be tax free, but using the Roth for venture capital or private investing seems a little wrong. 2 is just silly to me, and I blame lawmakers for that. No one needs $5b tax free, especially since you can't ever reach that with contribution limits.