Chicago526, I don't live too far from you, in Lake In The Hills. I know exactly what you mean about housing prices in the midwest not being as cheap as they once were. When DH and I got out of college, in 1998, we bought a townhouse in Schaumburg for 124,000. Beautiful, 2 bedroom, 2 bath, great location. But, once we were ready to move into a home, 4 years later, there was no way we could afford a home there. (A 30 year old home was easily selling for over 300,000!) We sold our town house for 180,000 (nearly a 60,000 increase in 4 years!) and moved west. (BTW, that same townhouse is now in the 270,000 range!)
We are now over an hour away from the city. A lot of our family and friends live in smaller homes closer to Chciago, but I like where I am....it's less congested and feels a little more open. Plus, I get more for my home. 3 years ago, we built a brand new, 4 bedroom, 2500 sq. ft home for 245,000. It was definitely a stretch for us, but we decided to make it work. Now, some of the exact same houses in our area are selling for 350,000. That's over 100,000 profit in just 4 years! I have no idea how this is happening, but I'm glad I got in while I could.
And yes, taxes are outrageous. Last year, I paid over 6,000 in taxes. DH and I often ask ourselves if we could live somewhere cheaper, but it's hard for us to leave family. But it just amazes me how far from Chicago we had to move to get a "decent" price on a house.
But I do know several people who got into the housing market early, bought their houses cheap and turned around and sold it for a huge profit. Some have moved into 3 or 4 houses in the last 10 years, all within a 20 mile radius of each house, just to make a profit off their old house for the downpayment on the nice new house. Their mortgage is also in the 3 digits, but their new house is worth 400,000+, is over 3000 square feet, and has every upgrade you can imagine. They just got in at the right time I guess, and used the housing market to their advantage.