Is it better to roll a previous employer’s traditional 401k into a Roth IRA or traditional IRA?

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Roll it to your new employer’s traditional 401k. Rolling it to a Roth IRA would require you to pay a likely quite large tax bill, so don’t do that. Rolling it into a Traditional IRA is the “traditional route” but if you’re anticipating ever clearing the Roth IRA income threshold (currently $140k AGI), and want to do the backdoor Roth, having a current traditional IRA balance complicates things. Simplest solution is to roll to new employer’s Traditional 401k.

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Do want to pay tax on it all now or not?

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If the backdoor continues to be an option and you do not already have an IRA, I would leave your 401k where it is or roll it over to your new employer. This assumes your salary is high enough that you are not eligible for a Roth IRA

Isn’t it better to pay tax now assuming we will likely have higher tax rates at the time of retirement? Is this the wrong assumption to make?

Depends on how much you make and what kind of income you want to pull in retirement

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