My total annual medical expenses are over 10% AGI, so I’m covered there. I learned that much before taking the early distribution.
Do you understand that only the portion of your medical expenses in excess of 7.5% of AGI will be covered by the medical exemption to the early withdrawal penalty for the Roth distribution?
In other words, let's say your AGI was $100K and you withdrew $10K from the Roth and put it all towards medical expenses. For the Form 5329 line 2 exception 5, you would calculate 7.5% of your $100K AGI, which would be $7500. You'd then subtract $7500 from $10K to get $2500. You'd end up with the following on Form 5329:
1 $10K
2. $2500
3. $7500
4. $750
So you'd be paying $750 in EWP to avoid filling out a few lines on Form 8606.
In addition, I looked at the Form 5329 instructions, and it is pretty clear that you should fill out Form 8606 Part III first to see if the distribution even exceeds your contributions or conversions in the first place:
"
Distributions from Roth IRAs. If you received an early distribution from your Roth IRAs, include on line 1 the part of the distribution that you must include in your income. You will find this amount on line 25c of your 2022 Form 8606."
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https://www.irs.gov/pub/irs-pdf/i5329.pdfBased on your description, it sounds like you wouldn't even get to line 25c of Form 8606, so you shouldn't even be filling in Form 5329.
So you'd be doing things contrary to IRS instructions in order to probably pay more taxes. I don't get it.