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Hey Jeff, A couple of ideas for you. First of all, since your net egg is heavily weighted to retirement accounts, you want to start some positions in a brokerage (taxable) account. The Roth and IRAs won't allow you to pull funds out until you are 59 and a half which hampers things for the FIRE crowd.

I'm 53 now and semi-retired. I am still working at a job I love (thanks to The Motley Fool), and only have to pull out about 1% from my savings to cover expenses for the year. BTW, my wife does work for the University of North Carolina and we get our health benefits through her employer.

We have about 30% of our overall funds in a taxable brokerage account, which will cover us under our current spending and employment situation for another 20 years. We could fully retire which would cut the brokerage account's ability to fund our lifestyle to more like 10 years.

How have we built up such a large amount in our brokerage? First, I always made sure we maxed out our contributions to the 401K, but only up to the match amount from our employers. Beyond that, I found it didn't make sense. I couldn't invest in individual stocks in the 401K, and the tax treatment of a 401K/traditional IRA (taxed like regular income) was worse than putting in a brokerage account and paying capital gains tax when you eventually sell.

If you are at a salary level where you could convert some of your money from your traditional IRA to the Roth (I think that's what you meant by Roth conversion ladder), that would be something to consider. We have 40% in our IRA, and 30% in our Roth. We plan to pull out of our brokerage account first, then the IRA, then the Roth. Ideally, we can stretch the limits until we are forced into RMDs (required minimum distributions). I think we'll be able to do that. Having money in all three accounts allow us to more or less control our tax situation for many years to come.

Rental properties can also offer a nice way to get some recurring passive income to allow you to put off pulling from stock accounts, but know that that strategy has risks too. The money you are putting into rental properties could be used to buy stocks in a brokerage account. Not sure which would be better for you. I've always thought managing rental properties was way more work than watching my stocks.

Dividend-paying stocks (in a brokerage account) is another way to generate passive income. I like my growth stocks too much to dip my toes into these kinds of investments, but the report below is pretty compelling.

https://www.thornburg.com/wp-content/uploads/home/pdfs/TH366...

Basically, it showed how if you had $1M in dividend aristocrats in 1990, you could have pulled out $50K a year for living expenses and end up with almost $15M by the end of 2019. Wow!

Hope this was helpful.
Brian
Fool One Guide and Fool.com contract writer
You can see my holdings here: https://boards.fool.com/profile/TMFBwithbike/info.aspx
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