Trying to understand a withdrawal plan.

Badger.....here a short and sweet discussion about SS taxation
Social Security: Taxable Portion of Social Security Benefits

I believe you may be mixing up 2 different concepts:
1) if have earned income from wages while getting SS, if you are less than some age (something like full retirement age which depends on birthdate) and earn more than some amount.....probably the number you mentioned in your OP, then your SS will be reduced by some amount dependent on your earnings.....this is earnings from sweat-of-the-brow work, not income from dividends, interest, etc.

2) This is separate from taxation of SS which is discussed in the link above.
Generally all your income + muni interest + 50% of SS is used to determine
what fraction of your SS is taxed. In the list of income you had in your OP,
most everything would be included except your cash bucket and your Roth and non-taxable TIRA distributions from non-deductible TIRAs (actually it's as Rita explained about pro-rata division)
(although possibly if you had taxable Roth distributions they might also be included....not sure about this one).
 
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