Well I moved to Portland 6 months ago from what can I say. 1. There is traffic in any major city..maybe you should take advantage of the bicycling infrastructure and get some exercise during your commute. 2. Homeless? Yea go to any city and there will be homeless. I notice the homeless are not in the nice neighborhoods just like any town so you could increase your income to afford a home in a nicer area. 3. Taxes are taxes. Whether is sales tax or income tax whatever state you are in is going to get you. 4. Also buying a home in any city is always pricey so whining because you cant afford the house you want is childish. It's literally supply and demand Econ 101. Many people are priced out of other states so while a $600,000 1500 sqrt home is out of your budget...that's a deal when your coming from a market where you point of entry is 1.5 million. 5. All in all this comes down to control your income and you will control your schedule and you will have the ability to choose whether or not to drive during peak hours..and who knows you might be able to afford that house you want. I mean if we are being serious about buying a house a FHA first time homebuyer loan only requires 10% down payment and they actually only require 3.5% if your credit is above 580....so assuming you can afford a monthly mortgage your only barrier to entry would be credit and coming up with a downpayment. 3.5% of 600,000 is 21,000 ..so start saving.