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You can't roll a 401k directly into a Roth. You have to establish a tradional IRA as a conduit. Then you can transfer that into a Roth if you wish.
If you contaminate your conduit or rollover IRA with even $1 of contributed money, it is nolonger a rollover IRA and you lose the right to roll it into a future 401k of a future employer. If you leave the rollover pristine, uncontaminated, you maintain that right. Since managing your own IRA is likely to give you lots more options than you have with a future employer's 401k, the value of that right is questionable, but that's a different topic.
Yes, you can have both a traditional IRA and a Roth IRA, and in the scenario you give it makes sense to do so. You can also have more than one tradional and more than one Roth. The paperwork and maybe the expenses mount, but you can. However, you cannot contribute more than a total of $2000 to IRAs for a given year, no matter how many you have. Best, Chris
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