And on a basic level, who cares if you are driving a Saturn Vue and someone else is driving a BMW, I know so many people who are "successful" and miserable.

If I tell you it is a bad idea, and you bish about that.. then you just are miserable little men. 

I personally tend to lean toward buy and hold SFRs that cash flow at least a little while they build equity, with an eye toward eventual appreciation.I did some research on Portland and found that there is lots of real estate on the cheaper side (especially compared to my miserable DC market) in the eastern more residential parts of the city, and also reasonable real estate in the suburbs. 

I admit that I have been guilty of this myself, when a dangerous and mentally ill tenant who was making our lives miserable got Section 8 and needed to move out. 

The time I failed miserably or the time I found success? 

I was miserable doing what I was doing even though it was and you can say still is successful.

Your boss makes your life miserable, meanwhile your friend doesn't even have a boss! 

I am getting good cash flow with very limited effort in the out of state properties.Like every other industry there are great providers and there are miserable ones so the key is finding a team on the good side of the scale.I would not suggest waiting to invest until you have returned to the states, especially if you have the ability to get going now and you don't have a time table for your return.

And any city will be miserable if you're broke.

Many sub 2 investors frame it as foreclosure rescue.Many others frame it as "no money down" investment as in the Porter case, took over 40 properties sub 2 to rent out, some on lease to own deals, failed miserably when tenants fall behind on rents, and she couldn't pay the sub 2 mortgages.