I have always considered condos more of a lifestyle choice than an investment.

I currently work full time in financial services servicing mutual funds.I have always been interested in real estate, seeing it as a way to build passive income, and a lifestyle that has more freedom than the long hours working in corporate America provides.

I see investing in real estate as the quickest path to early retirement, with my definition of early retirement being that I do not require a W2 job in order to pay for a comfortable lifestyle.

For recreational and lifestyle properties I am interested in Leavenworth WA, Westport WA, and Bend OR.  

South of SR 2 is mostly flood plain, then it's King county (where Seattle is located) and much higher prices, even though the commute to Seattle is about as long.The lifestyle quality north of Seattle is much better than the areas to the south.

The more comfortable you get to feel about real estate, the more you understand it, the more clear you will see what direction is possible for you even advantageous for you or simply what fits with you, your life style and your own personal financial picture. 

As rents continue to escalate I believe the land developers will be enitced to return to the game because some the rent sticker shock will exceed lifestyle presences at some price point.Schillers definition contains an element of subjectivity.  

One property isn't going to change their lifestyle and they need to diversify over a portfolio of properties so that when they have a problem child, they don't have all their eggs in one basket.

I am single, no kids, little dept, and a modest lifestyle. 

As Shawn pointed out, many of these houses are old and may be higher maint in the long run, the upside being that they are close to the city and boomers are increasingly willing to pay a premium for an "active" lifestyle in a smaller home close to the action rather than a larger home in the burbs.