I have a couple of great clients who have rented in the Lakeview East neighborhood for quite some time. They really wish to buy in this area of Lakeview, east of Halsted.
What is interesting about pricing in this neighborhood is how "tight" it is. The demand is consistently strong for this area regardless of the national market. The neighborhood is not a speculative buy... it's about living in one of the greatest cities near the lake, entertainment, restaurants, and with diverse people.
It's pretty easy to tell, for the trained eye, what is offered at the top of the market and what is offered in the lower quarter... the deals! This is also true for Lincoln Park, Lincoln Square, and the River North where housing stock is consistent and people buy less as an investment but more to live in and enjoy what the city has to offer.
If you're stretching for these neighborhoods... take heart. It's generally less of a risk and you'll live in the neighborhood you truly love.