I have no clue how or why specific bikes are better than others, so I'm gonna have to trust you guys. I'm thinking about doing bike4chai this year and I need a bike.
1) what price range will a good bike for that be. (Mind me, I'm a galitziana, so keep it in my budget)
2) being that I'm going to shell out a nice amout for this, where can I learn how bike specifications effect the cost a experience of cycling.
3) where to buy? (and any ways to manipulate a deal?)
First off, congrats on deciding to do Bike4Chai. It's an incredibly fun and rewawrding experience and you're going to feel so accomplished.
As others have mentioned, it's just not worth it trying to buy a cheap bike online. It'll be fine for your first month or two but you're going to regret it very quickly. It won't fit you very well (and 3+ hour rides on a bike that doesn't fit will be painful). Addtionally, the components will start falling apart and you'll end up spending way more time and money getting things adjusted or fixed than if you had just gotten an entry level road bike from a real bike shop (first hand experience because my first road bike was from a big box retailer).
B4C riders get discounts (~10-20%) at several shops so depending on your location, might be worth checking them out. Lots of places also have fairly steep discounts at the end of the season( mid-august through septemeber) or at the beginning of next years season (march-april) because they're trying to clear out inventory so it's worth stopping in your local shop and just asking if they have anything on clearance or any floor models on sale. As others mentioned, you can also look for secondhand but DO NOT just buy off a random person on ebay or craigslist. There are tons of fakes from China that don't have the same type of quality control and the last thing you want to be worrying about is your frame literally falling apart while you're flying down a hill. Extremely dangerous and not worth it at all. (
http://www.bicycling.com/bikes-gear/components/catch-counterfeiter-sketchy-world-fake-bike-gear). A reputable shop should be able to spot a fake very quickly so its OK to buy used from a place you trust but don't just go on Ebay looking for a deal (as a DDFer, I'm sure it's already crossed your mind
I would disagree with what others have posted above - if you're trying to get the cheapest bike possible, you definitely don't need a carbon bike. Sure, if you have the money and you're in tip-top shape, carbon will definitely make a difference but if you're just starting out and looking to get the biggest bang for your buck, I would stick with an aluminum frame. The difference between a steel frame (what you get from walmart, etc) and an aluminum frame is ginormous but the difference between an aluminum and carbon frame is only a couple pounds. If you've trained enough (B4C makes it easier with plans, group rides, etc) the little bit of extra weight won't make a difference on your rides, and if you haven't trained enough, the carbon bike won't help you at all. Do NOT be intimidated by the "pros" with their fancy bikes that you're going to see while training or even on the ride itself. I've come first place in a 60+ mile race on a 30 year old steel bike and as someone said to me at the finish line, "its not about the machine, its about the engine behind it."
No matter what bike you go with, there are three things you definitely want to be getting because they make a huge difference. First one is obviously a helmet. Secondly, are proper shoe + pedals. They take a bit of time getting used to but make a huge difference on longer rides and once you've ridden with them, you won't be able to go back. You should be able to get decent shoes for ~$50-$75 and pedals/cleats for another $40-60$. Worth every penny. Third item is clothing - specifically biking shorts and jersey. Even the cheapest bike clothing will make your riding a lot more comfortable. You should be able to get both shorts/jersey on amazon for < $50.
I bought my bike outside the NY area so not sure the exact price of bikes but I think you should be able to get everything above for ~$1,000.