We are in a similar boat, although my husband is 58, and I'm 42. There is no way his current 401K balance is going to sustain us when he retires. He started it way too late in life, for valid reasons that i won't bore you with.
Several years ago, when the stock market was doing well, I might add, the folks who manage his 401K had a "check-up" meeting with hubby. They showed him all the fabulous things he could do with his 401K and how much he could make. When they were done, he handed them spreadsheets outlining the returns we're making from the real estate investment business (mostly rentals, some flips) that I run. After a few minutes, they looked at my husband and told him to give all the money to me because I was making at least twice what they could ever offer him with their products.
At the time, we did not need to pull the 401K. Now that cash is harder and harder to come by, we've decided to pull all of it out when he turns 59-1/2, thereby avoiding such a loss as was mentioned in previous posts.
I've looked at Roth IRAs, and I just don't think they're a good fit for me. I've never been a big fan of indefinite deferment--just letting my descendents pay the taxes when I die is not a good idea to me. First of all, I cannot afford to be tied down to so many rules and regulations that surround such investment accounts, including not being able to do any work yourself (I do very little myself, but still...). Then you can only pull out the principal? What's the point? I do this to make money. When I'm done with an investment, I want the the option to do whatever I want with the money I've made. Usually, we just turn around and reinvest it (the initial investment AND the profit) into the next properties. But sometimes I want to skim a little off the top for some project on my own house or something else. I want to enjoy SOME of the fruits of my labor now--just a little bit. These other investment options don't give me the freedom I need.
For the same reason, I am not at all interested in 1039 exchanges.
I'm sure I'm missing some important information, as I am far from an expert in things like Roth IRAs and such. I promise, if someone makes the case that they are in fact a viable and healthy option in my situation, I'll jump on the wagon ASAP.
In the meantime, I can't wait to get my hands on that 401K money next year. I can do some serious investing with that. In fact, we've already calculated that, with the # of rentals I can buy with that money, together with the properties we already have, the rents from all of those properties will replace my husband's income 125%. Everything else is cream. He'll be able to retire before he is 60.
That's the plan.