Thanks for the reply Carl, appreciate you taking the time on this
The strategy laid out is sound, however it isn't really applicable for me since the conversion won't move me into a new tax bracket. My primary concern ties back to your first post about underpayments and quarterly tax payments. If I do a $20K conversion in Q1 of 2019, up my withholdings on my W4, and still owe by the time I file my 2019 taxes, have I introduced any additional risk or cost that I'm not thinking of since I'm underwithheld over the course of a year? I'm primarily concerned about underpayment penalties
For background, I converted $20K in 2018, but did not up my withholdings, and as I work through my taxes, I'm going to be underwithheld in 2018, but I will pay the entire amount before April 15 2019. So by the filing deadline, my balance will be zero. If I do the same in 2019, with the same situation (convert $20K, underwithhold, pay the entire balance by April 2020), will I run into an issue? I've seen that 2 consecutive years of owing large sums at tax time results in an underpayment penalty, but I read that as only applying to folks who do estimated tax payments on a quarterly basis. I do not do quarterly estimated tax payments, although maybe I should be?
