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1. When you roll 401K money into an IRA and then years later want to move it to another fund, is it onsidered an transfer from an IRA to another IRA?

Absolutely... and you can do this as often as you want, as long as your new custodian transfers the money from your old custodian, and you don't touch the money. You can split this money up into as many accounts as you want.

2. Can I then add to the Health Fund from money that is in another IRA (created from a rolledover 401K)or would I have to open a different Health Fund for this?

Yup, you can combine IRA accounts, too. The only reason why rollover IRAs are segregated, is so that you can roll this money into another employer's 401K. Since that is not Foolish, don't worry about it.

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