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Welcome to the chainlink!
The best option for you or anyone would be to maintain a relationship with a good shop in your neighborhood, but in lieu of knowing what part of town you're in, I'll offer:
I was at West Town Bikes last night and noticed Ciclo Urbano ( http://www.ciclourbanochicago.com/ ) was well stocked with refurbished/reimagined bikes.
By "collectives" I believe Eric was mainly referring to Working Bikes ( http://workingbikes.org ) however for all the good they've done for bicycling in the past, that may not be the best option for you since you'll likely need to put some work into the bike once you buy it to get it working really well (that goes for craigslist too.)
I don't know that any shop really does trade-ins, but you can certainly ask.
My only advice is that if you're not sure what size bike fits you, let bike shop employees help you, but stick to your guns and don't buy a bike that doesn't seem totally fit for you on a test ride, no matter how much anyone swears it's the perfect size for you.
I love bike shop employees and do not think that anyone has ever been anything but well-meaning to me, but I have all sorts of terrible memories of people putting my short ass on 50cm frames and saying "This is perfect for you!" and then wondering why I was falling off of it and impaling myself on the top tube at every stop. When I finally found my bike (a much smaller 44cm frame) it was like magic. Birds sang, angels strummed their harps, fireworks went off. It was magic.
Basically, when you find the right size bike you'll know, and do not let anyone convince you otherwise. I do not want to see you end up on another bike that doesn't fit you.
PS- I am too hangover at the moment to explain how to measure standover height and such to figure out what size bike you should be riding but I am pretty sure Mr. Google could direct you toward the pertinent info
The best thing you could do is call some bike shops that provide an actual fitment service. You don't necessarily need to buy the bike from them, just use it to find out what the best dimensions would be. A lot of people seem to think that a good fit is determined by their ability to straddle any given bike without contacting the top tube, but this is a woefully inaccurate method. Arm and torso length, inseam, thigh length, and other bodily dimensions all factor into this along with the type of riding you will be doing. Once a good baseline frame fit is established it should then be fine tuned by saddle height, angle, fore and aft position as well as handlebar stem length and height, crank arm length, etc.
Standover height has very little to do with true fit. I ride a frame that many would consider "too small" (I'm 6-1 and ride a 57-58cm), but I do not like the feel of being "stretched out" on my bike (which a 60cm frame tends to do). Check this, if you have a lot of time :)
Standover height has very little to do with true fit. I ride a frame that many would consider "too small" (I'm 6-1 and ride a 57-58cm), but I do not like the feel of being "stretched out" on my bike (which a 60cm frame tends to do). Check this, if you have a lot of time :)
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