No. of Recommendations: 2
I agree with one of the prior comments about it being good to have you assets in a mixture of account types for flexibility and to be adaptable for future tax law changes. If you don't already have a significant percentage of your net worth in taxable account then it would be good to save up more in the taxable accounts for diversification.

....So, is there a reason that I A) wouldn't put something into the IRA every year even if I have already maxed out my 401K and B) Wouldn't convert what I have now and what I had every year from a traditional IRA to a Roth IRA?...

It wasn't completely clear but it sounds like you are talking about what is called a "back door Roth". If you google this term then you will find lots of information like this.

The non-deductible IRA's that are not converted to a Roth have at least three major drawbacks.

1) If you retire early your ability to withdraw the money without a penalty is restricted.

2) They will be taxed at your ordinary tax rate, instead of the capital gains tax rate.

3) If the alternative is owning stocks, then if the stock goes to your estate or gifted to a charity it will be at a stepped up cost basis and the capital gains taxes will never have to be paid.

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