Hey Guys
I've been a Realtor for 17 years, and I want to offer my 2 cents.
First off, I'm not big on homeownership right now, for me. I had the house on the hill, exotic cars, everything... and lost it all. I'm not reaching for the brass ring, or the American dream. For that matter, my ex-wife wiped me out and I'm just now getting back on my feet. Shit economy didnt help.
I don't like having so much to lose, so much to worry about.
I did like the suggestion in this thread about buying a place in the Phillippines, for instance, sitting tight here whilst paying it off, and then moving for good or use it as a second home, whatever. Problem with that is, what if you get sick of the Phillippines?
So, I offer another approach, which I may well execute myself over the next few years:
Why not get a shitty/basic little condo around 40 to 50K? Preferably a 2 bedroom, and at least 1.5 baths. You also want washer/dryer hookups and maybe some kind of balcony/landing. It doesnt matter if its in a lower-end area. Live in it, with a mortgage (assuming you couldn't pay cash) and focus your efforts on paying it off. Make 40k a year? Focus half of that on paying off your condo. In 2 years or so, its paid off.
Forever.
Now, go buy another condo just like it. Maybe even in the same complex. Get good at snatching a good deal (I can offer more on this) and repeat. Another 2 years, another paid-off condo (use the cash-flow from the first rented-out paid-off condo to accelerate the payoff on the 2nd one)
Now you own 2 condos, free and clear. Why not do this once more? Get a 3rd condo. Focus on getting it paid off, and focus all your cash-flow from the other condos to pay it off.
5 to 6 years, 3 condos owned free and clear.
This is low-risk because anyone can afford the payment on these, even with a shit job, so you can't lose your ass if your job tanks. Further, because they are condos, there are no roofs to fix, nothing. No maintenance outside an occasional toilet tweak.
Now, you'll always have somewhere to live for the rest of your life, and don't have to answer to any landlord or mortgage company.
Ready to ex-pat or travel extensively? Great!
Get a prop mgmt co to rent out the three units and wire the proceeds into your account every month. Since there are no mortgages, the monthly proceeds from 3 condos will be respectable.
Move to anywhere you want in the world, and enjoy your retirement.
cheers.