It sounds like you're concerned about having enough properties to choose from and ensuring that you get a good deal. Surely you're aware that virtually the entire country is in the throes of a buyer's market? Ask your agent to calculate for you the absorption rate for Bucktown/Chicago and you will have the answer to your question.
I'm really trying to get a sense of whether or not I can expect to see new listings come up over the next several months while I'm in temporary housing, or if the apex of buying season is already upon us. I've been scouring the listings and I'm not seeing a whole lot of new properties (in my price range, desired area and features, etc). Temporary rental housing is not an ideal choice for me, but if the supply of properties typically continues to replenish even into the Fall it may be worth toughing it out until then.
So, my refocused question is:
Aside from the people selling properties because they have "no choice" (e.g., distress, job-relocation, etc.), do people in Chicago continue to put their homes up for sale (new listings) when the weather starts to turn for the worse? Or do they hold off until the next selling/buying season?
I know this is a tricky, loaded question, but I'm fairly new to Chicago and the quirks of the RE market here.
(BTW, I do have an agent.)
You just have to know specifically what you want and or need. And how much you are willing to spend. And then, go after ONLY that.
If you need a home in 3 weeks, unless you are prequalified, you may seriously want to look at renting or rent with option.
If I can help in any way, please feel free to call or email me!