To answer your question in one sentence, the move was very strategic and we have not regretted it so far.

For instance we wholesale, rehab and occasionally (when it's strategic for us to do so) list properties.

This is just something that I have to think about strategically as well as emotionally, given my long-term plan.So, should I spend a little more time/money shopping around for a place that I LOVE or do I shop with my head and go for the property that will work for now, and make a nice rental in a few years?

Plenty of very unhealthy people have incomes.Wealth is a strategic placement of funds, calculated decisions, and educated spending, saving, and investing that all equal a system in which one considers themselves "set up" to enjoy life without the constant hassle of making ends meet.Theoretically one could flip houses for years, earning well into the upper echelon of tax brackets and still not be wealthy, or be completely wealthy, depending on how they see the daily activities of their lives as either a job, or a hobby that pays well.But to get right down to what I think you're asking Christy, is "what is the best approach to wealth?"

You also have to do your due diligence on unemployment rates, population growth, job market, property specific location - is it strategically good location, and ALWAYS, ALWAYS when purchasing the property analyze how easy will it be to sell it for profit?

@Megan Shay has a good point about the Kitsap area, but it's steadily climbing as well and you'll need to be strategic.

Some people use the short sale strategically, and it can actually make a lot of sense if you are ok with credit score dropping 100 points, and waiting 2-3 years for repair (if you do what you are told by a loan officer/credit counselor).  

Once repaired, put it on the market. maybe consider some strategic but low-cost upgrades like paint/flooring/backsplash/ inexpensive bathroom/kitchen upgrades to make the unit  pop and sell for top dollar (get your agent to make some recommendations on what they think would make it pop in your market). good luck!

I have a friend (we'll call him Joe) who is considering doing a strategic default on his home.Although it's a struggle, he makes enough to pay his mortgage.

So, it may not work all the time.I am not really a NPN buyer, but I will buy them for strategic purposes with a goal of acquisition.