@Sandi_k Thank you! I think you answered my basic questions - so I can treat my IRA like a 'regular' account when I get to the drawdown phase (I was wondering if the money is literally divided into 'interest'/principal and I would have to tell Vanguard which dollars in which bucket I was choosing [silly, I know]), and that I will treat it as regular income, file taxes "as normal". That makes so much more sense now!
@reeshau I'm following the investment strategy laid out here on the MMM forum: 401k to get the match, max IRA, throw everything 'extra' at my 401k (to max each year, but I think that's more of a dream). Once I max both the retirement accounts, that's when I'd be looking at opening a taxable account - with Vanguard, I guess? And so that's where dividends come into play (there aren't any 'dividends' to draw from on my IRA? Its all just one lump of money?) << This is where I start getting confused!
Everything you withdraw from a traditional IRA is taxed as income. There's no distinction between original contributions, capital gains, or dividends. I think the idea is to make it sort of comparable to a brokerage account from a tax perspective. When you contribute to a brokerage account, you're doing so with already-taxed dollars, dividends are taxed as they come in, and capital gains are taxed when you sell shares. Thus, each component (contribution, dividends, gains) gets taxed once, and only once, but at various times. For a tIRA, none of it gets taxed taxed until you withdraw them, and they all get taxed at the same time. As a result, there aren't any "buckets" in a traditional IRA
Nothing you withdraw from a Roth IRA is taxed at all.* It doesn't even show up as income on your 1040 form.
* - All of this, of course, assumes you wait to withdraw until the year in which you turn 59.5. If you withdraw earlier, you pay penalties.
To get money out of your retirement accounts, you'll just initiate a transfer by either calling Vanguard or doing it through their website. At the end of the year, they'll send you a 1099-R (if I recall correctly) with the numbers to use when filing your taxes.
Now, if you plan to retire earlier than age 59.5, and have most of your savings tied up in retirement accounts, it gets a bit more tricky, because you can't access those funds directly without incurring penalties and extra taxes. That's where the Roth Conversion Pipeline aka Roth Ladder comes in. It requires you to have five years of spending money in accessible locations (usually some combination of brokerage account, Roth contributions, cash, etc). If such early retirement is in your plans, you'll need to make sure you fund those buckets sufficiently.