What would be the most productive way to spend 20k?

[Michael Johnson]

If you had 20,000... and this was your one and only shot. How would you escape the rat race?

p.s. I want vacation homes, but answer however you'd like.

[Kevin Siedlecki]

@Michael Johnson. Here's what I would do. There are definitely other strategies, but this is the slow and steady, safest route (in my eyes). Since you said this is your one shot, you want to give yourself the best chance possible to succeed. It's about a 5 or 6 year plan:

Year 1: Find a 3 or 4 unit house, and finance as much of it as possibly with an owner-occupant residential loan. Stay in the rat race for a couple more years while you save up for another house. 

Years 2-3: Repeat. Buy another one the same way, move to that one, and rent out the first fully. At this point you are living for free and getting some significant cash flow. 

Year 4: Depending on how well you did with your purchases, and how well you're paid for your job, either repeat a third time, or buy another property as a pure investment. Putting 25% down on a fully-rented property will create more cash flow for you.

Year 5: With at least 2 cash-flowing properties and one paying for you to live for free, you might be able to quit your job. I wouldn't, though. Get at least one more, again either as a house-hack or pure investment. 

Year 6: Now, again depending on how well you did making your purchases, with at least 3 cash-flowing multi families and no housing payment for yourself, you should be bringing in enough cash to live off of.   

I know this isn't a glamorous answer, but it's the answer that gives you the best chance at success. I would be interested to hear what others have to bring to this discussion, if they have faster or better ways that don't depend on getting started by putting that $20k into a phantom perfect flip.