@Daniel C.
I’m in a similar situation, with around 50k (a little smaller than 250k 😃) in a 401K, getting ready to switch jobs in the near future. To be frank it’s basically a no brainer.
You absolutely have to cash in the old 401K to buy cash flowing properties. If you were buying a Lamborghini that would be a different story.
Reasons why:
1) you will eventually have to pay taxes on it at some point. Wouldn’t it be better today because you know what tax bracket you’re in and how you will be taxed. Who knows what the rates will be in 20 years and what tax bracket you’ll be in at that time. And just to be clear who wants to be in a lower tax bracket during retirement? - not me.
2) build your real estate portfolio now - why wait and let your capital sit in some account when you could use it to build your empire now.
3) there are no guarantees in the stock market. Who knows what the return will be when it’s time to retire.
4) You probably aren’t losing any of your money. For example if we ignore the market return and say your initial investment was 125k and your old employer matched the 125k you would still be ahead after taxes and the penalty.
I’m a bit surprised on a real estate website so many people would advise anything else. People see the words tax and penalties and become timid on the other hand words like closing costs and points are accepted.