I checked your pointer. The flowchart is excellent. The part that has me concerned is in the points on the end of that same page 63. If IRC, my internet source talked of the additional 10% penalty rules especially concerning a 401K conversion and a Roth 401K conversion not being the same as an IRA conversion.
From your link:
"The 5-year period for determining whether the 10% early distribution tax applies to a distribution from a conversion or rollover contribution is separately determined for each conversion or rollover contribution, and is not necessarily the same as the 5-year period used for determining whether a distribution is a qualified distribution."
The link that you provided then gives an example that is clear as mud that indicates that year basis is not the same. I am not a tax expert, but where the flow chart giveth, the fine print seems to taketh away. The ramifications of a mishandling is too costly for me to blithely assume that I have covered bases needed for that IRS audit. Been there, did that once and won, but really don't wish to repeat the hassle...ever. This is one that I want to check with a much better tax expert than I am
As Alan pointed out, this is the internet and anything goes so you should definitely be careful. This is an interesting general problem......how does a (relative) layman evaluate an expert's competence in a technical field? Does paying for an answer make it better? Does paying more make it even better/more likely to be true. What if you get 2 differing answers? I don't know the solution but I can appreciate the problem.
Not the whole answer but a piece......I would at least learn something so that if the advisor says something that I recognize as wrong, I can probe deeper.
Also recognize that esp. on the internet, this can be a shared responsibility between questioner and answerer..... the answerer will attempt to work on the apparent question. If the questioner leaves other relevant info, the questioner may not realize it. E.g. AFAIK, your reference to 401K/Roth 401K was not in your original post?
A suggestion (and it's free for good or bad)......ask your question w/ all the gory detail whether you think it's relevant or not at the fairmark.com forum (retirement sub-forum). Look for a reply by Alan S. I would bet a fair amount on his answer.......but in all honesty, it's the same dilemna I mentioned in the beginning. How do I (the layman) know he really knows his stuff?
Another tidbit......the section you mentioned has this in the beginning:
Additional Tax on Early Distributions
If you receive a distribution that is not a qualified distribution, you may have to pay the 10% additional tax on early distributions as explained in the following paragraphs.
To me, that says that the 10% additional tax may apply to a non-qualified distribution. To me, that also implies that if the distribution is qualified,
the 10% additional tax does not apply..............however, it does not actually state the latter so if you are a worrier, there is cause.
I agree w/ you that the passage is clear as mud.....I believe it is pointing out the the 5 yr master clock from when the first Roth was opened is not necessarily the same as the 5 yr clock for each conversion that applies when you are < 59.5 and taking distributions.
Good luck!
btw....how did you quote that section from pub 590. When I try to copy and past from there, my computer highlights both columns and the lines get intermingled.