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Greetings, Rich, and welcome. You asked:

<<Now, neither of us cares if we roll our former 401ks into another, some day. We would like to combine/add to these funds in a Foolish way. Can I roll my recently rolled over money immediately or is there a waiting period?>>

There is no mandatory waiting period on moving money from one IRA to another IRA as long as you use a direct transfer of the funds from the old custodian to the new custodian. You may do that as often as you like. All custodians know how to do this. Just ask the new (or target) provider for the necessary application and transfer instruction forms, fill them out, send them back, and wait for the money to be transferred.

<<Is it best (or even possible) to roll the money into a new IRA gradually, or is it best to go for the full monty?>>

Yes, it's possible; however, you will have to complete a transfer instruction form each time you wish to do so. What's "best" only you can decide based on your investment desires, knowledge and willingness to accept risk in the desired investment.

<<How should I handle the old IRA and the annuity? >>

Again, that's entirely up to you. Be aware, though, that if you surrender the annuity you may encounter cancellation fees that will be imposed by the insurance company. Know what those will be before you do. You may want to wait until they disappear before you do anything, so that means you must know what's in the contract.

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