My 17 yr old son went in for a fitting last night. He wants his first road bike.
His biggest gripe when we moved to the country was biking. He lived on a bike in the neighborhood but he will hardly swing his leg over one in the country. He has never been an off-road bike fan.

He has an unusual athletic history.
He was a gymnast from 2 1/2 to 11 yrs. Had to quit because he was just way too tall. This was very depressing for him as he mentally considered himself a gymnast and could not remember a time in his life when he wasn't going to the gym. He floundered physically and lost his incredible physique.
Then he discovered ice skating at 13. I pushed for figure skating as it was a logical extension from gymnastics but he didn't want to do another sport that would get him called a "sissy". He chose hockey. Expensive mistake. He has never developed that team sport mentality. Dropped it and after a few months sheepishly approached me and asked if he could take figure skating lessons. An enthusiastic "yes" was my answer.
Went well for several years and then our rink closed for four month. We had just purchased $650 skates. He had a 4" growth spurt during the off months and grew out of the skates. He lost his skating heart and the physique took another dive.
His older brother had taken up rowing and was trying to entice him to do it as well. Since he is so stubborn and didn't want to be a copy-cat he refused. I forced him to go to the rowing camp last summer and he fell in love on the first day. Now I have two rowers to watch at regattas! His physique is on the fast track back to his gymnastic days and he has made it over the hump where you no longer have to push yourself to exercise but your body tells you that you must exercise. He wants to cross-train and what could be better for rowing than biking?
Nick is pushing 6'4" at 17 and is a very late bloomer. I think he has a few more inches in him. My dad was 6'7" and grew into his 20's. My husband is only 5'10",the late bloomer gene came from him and he also grew into his 20's. He is has a thin build but is not a bean pole.

Nick measured for a 63cm. All adjustments can be made in the optimal range at this time. At what height does it get difficult to fit an off-the-rack bike?

Our favorite LBS is a Cannondale store and we are looking at a CAAD9 5 for his first bike. We want to stay in the $1500 range. The shop can get a new 2008 Six with Dura-Ace for $2300. We are in a huge quandary. The USA made carbon frame and component upgrade is a huge plus and what if he gets bitten by the competitive bug? He could outpace the $1500 bike quickly. You should see his legs from rowing alone!

He also is back at the rink. On hockey skates but not playing. He loves speed. My husband estimates he skates 40 miles each Saturday. I wish we had speed skating here.

His birthday is not until November and it is hard to justify such a huge expense mid-year. We do love to support our kid's fitness and academics. But there is always a limit.

Another bonus, our kids have near zero sibling rivalry. If we spend on one the other does not expect a balance on his side or feel slighted.

So, any suggestions or experiences to share about passing up the good buy and regretting it or buying more bike than you will ever need and regretting it? Or the opposites and being thankful for your decision?