Lesson 4: Kick the Tires.
Before you take that semi-shiny used ride home, you want to ensure it's in excellent condition.
After you've given the bike a good once over and it meets your current criteria (right size, bitchin' looks), take it for a spin. Shift through all the gears to test the drivetrain, and take it on varying surfaces to make sure it's stiff where it needs to be but can still absorb the road's imperfections.
After that, look for any cracks in the fork or frame. Even the slightest crack can grow and eventually cause something catastrophic.
Lesson 5: Buy a Bike with Name Brand Components
While small and insignificant to passersby, components are half a bike. Making up a bike's brakes, derailleur, gear shifters, crankset and chain, this is the bike's engine. And you wouldn't buy a car with a defective engine, would you?
With that in mind, make sure the components on your bike have a name brand associated with them. Shimano, SRAM, and Campagnolo are all brands that make fantastic groupsets. If it's Bob's Components, you might want to look elsewhere.
Also, while the components may be name brand, they could still be "budget" components and not the quality you're looking for. And unless you're a gear-obsessed roadie who attends Interbike every year, you won't know the name of every groupset of every manufacturer. Which brings me to my next tip:
Lesson 6: Do Your Homework.
While the Internet is full of scammers, it's also our greatest weapon against them. Before laying down that cash or swiping that card, get online and see what others have to say about your bike model or components. Roadbike Review and mtbr are great resources that include user reviews and specifications for bikes of any manufacturer and any era.
Now, whether you're getting a good deal on a bike or not is another issue. While there might not be a Carfax for bikes, there is, however, a bluebook for bikes.
The aptly named Bicycle Bluebook will tell you whether your bike's seller is a snake or a saint. And while I found the site to undervalue bikes just a smidge, it will give a good ballpark estimate as to your bike's worth.
Lesson 7: Be Patient and Use What You Know
Contrary to your coolest fantasies, bikes don't fall from the sky. To find the bike with the right look and feel could take weeks or even months. But keep plugging away, as that aero road bike preposterously ridden once a week to a church around the corner is out there, waiting for you.
But the most important thing I learned in my month-long search for a bike is to use all of your resources. Whether it's friends, books, colleagues, the Internet or this article, the knowledge you gain is an enormous asset when finding the right bike.
And me? Well, after scouring bike shops, reading online forums and incessantly refreshing Craigslist and eBay, I finally found a bike that suited my needs at the right price: a LeMond Big Sky SLT. While my more serious cycling friends will undoubtedly poke fun at the angled stem and super comfortable geometry, it's a bike that suits me, and that's all I wanted.
Ready to ride? Search for a cycling event.