The Big Question: What Kind Of Bike Should I Get?

I think I have an average amount of friends, family and acquaintances. I'm not going to count them because I don't care and you sure as hell don't. It's probably a fair amount of people. I thought about this number just now to illustrate the point that a very high percentage of those friends,  family members, coworkers etc. have asked me the same question which is usually is the beginning of the same conversation.

Person - Hey man,(son, bro, pal, coworker, handsome, dipshit...) I want to get a bike, what kind should I get?

Me - What do you want to do with it?

Person - Well I'm looking for a pro-level all mountain big dropping race ready road bike to do cyclocross centuries on while I pick up the kids from the downtown grocery store on my way to do a two night bike tour with the rotary club.  

Me - Awesome! How much do you want to spend?

Person - $250

Me - No.

Person - Huh?

Me - NO! Spend more money on bikes. You'll be happier. 

Person - No.

Me - Huh?

Most if the time this is where the conversation ends. If prodded I usually  recommend a Surly of some shape and size. I've had two Surlys, I love them, and they are a good bang for the buck. The problem is my idea of a good deal doesn't jive with most civilians.  To me, $1100-ish for a bike that will never quit you seems like a pretty good deal.