Contributing to both the Roth IRA and 401(k)

[Big TR]

Yes, your personal money helps. You asked if you were missing anything. That was just one thing I could think of.

Also, you need to have cash sitting around to pay the taxes on the conversion. Let's say you have taxable income of $75k and convert $30k of the IRA to a Roth. This is taxed at the 28% rate. You will have to come up with $8,400 for the Feds, plus X% to the state, to cover the additional taxes you will owe on the conversion.

You must then consider if you will be in a lower tax bracket than 28% upon retirement.

There are a lot of things to factor in when converting to a Roth that not everybody takes into account.