Is there a way to rollover my 401k from a previous employer into an IRA that, upon retirement, pays me monthly and can be willed to my son?

You can roll your 401(k) into an IRA. The arraignments for payments later are 100% unrelated to the rollover.

You can rollover a 401k.  As for monthly payments, that is not generally how it works.  If you want monthly payments, look into an annuity.  You can Will it to your son and you also list him as the beneficiary.

My wife and I are doing exactly that. I had a TSP with the federal government. As soon as I retired, I rolled it into my existing IRA.

My wife had 401k plans with three different companies - when the previous employment ended, she kept the plans and they did quite well with the money that was in them. When she retired from the third company, she rolled all three into her existing IRA. If you don't have an IRA, you can open one and roll the 401k into it.

We each are now drawing a monthly paycheck from our IRA accounts - which are professionally managed by a fee-based advisor. The fee is well worth the money. We would have to make all the investment decisions ourselves, figuring out what things to sell and when, to maximize return and still pay us our monthly income. We are following the 4% rule and we will not outlive our savings barring something catastrophic.

We are each other's beneficiary, and whichever of us goes first, the other can roll the remaining balance of that IRA into their own, and then would choose a new beneficiary, who could inherit the money.

So you can pass what remains in your IRA to your son WITHOUT A WILL. Just make him the beneficiary of your IRA.

This 'insurance' you are talking about sounds like an annuity. I recommend staying as far away from annuities inside of an IRA as you possibly can. NO fee-based advisor would recommend one to you. PLENTY of commission-based salespeople will, because it puts a nice commission in their pocket.

When your son inherits the IRA, the IRS wants the taxes that you deferred all those years. He can take the entire amount and pay the significant tax bill. Or he can defer the bulk of the taxes AND continue letting the bulk of the money work for him until he retires. He can open an 'Inherited IRA' which will have both your names on it. He will be required to start taking money out every year and pay the tax on it, but he can take a payout based on his life expectancy instead of yours. This keeps his yearly distribution, and the tax on it, small.

However, an inherited IRA cannot be put into another inherited IRA account. His beneficiary on that inherited IRA (from you) will have to take the entire amount and pay the tax on it. There are ways to eliminate that from happening - we did it with the IRA my wife inherited from her mother, and now all of that money is in my wife's IRA - but it's too complicated to explain here. A good financial advisor will know how.

I think most kids behave that way. It's normal. Gotta get used to it tho.

I think you are trying to describe an annuity.

You can purchase an annuity.  You wouldn't want to use your 401K money for this because it would involved a full cash out.

What to do with your 401K, when you retire:

- roll it over to a 401K

- establish your son as the beneficiary of the 401K

- setup monthly allocations (monthly withdrawals); this can go directly to your bank account as an automatic deposit.

- when you die, your son with get the remaining money in the IRA

If you are over 59.5, then you owe standard income tax on the IRA withdraws

If you are under 59.5 you will owe income tax and a 10% penalty. 

Nothing prevents you from buying life insurance and naming your son as the beneficiary.

You can certainly use the retirement money to buy an annuity that pays you a monthly amount.  Some plans ensure that you either receive a certain amount of money or that some passes onto heirs.