My brother is constantly looking to buy luxury watches. (he already owns 4 or 5) He consults me about every one of his purchases because I have a large collection of watches, including some higher value vintage pieces. The funny thing is, for me it is just a collection that I don't think about 99% of the time, while he sweats it daily, or at least weekly. Should he get a Patek Philippe Calatrava, a Jaeger LeCoultre Reverso. or maybe an Audemars Piquet sports model? Which watch will make just the right impression on his clients, and which will best round out his collection? Similarly, he agonizes over whether to wear his stainless Rolex Datejust, or his gold one, or maybe his Daytona on a leather strap to this business trip or social occasion?

Here is what i tell him. They are all just jewelry for men that also tell time. The average person either can't tell the difference between a $20,000 luxury watch, a $200 department store model, and a $20 knock off, or just doesn't care. So buy/wear whichever one you think goes with your suit, or alternately, whichever one you feel like wearing.

Similarly, your quest for the perfect bicycle for every occasion seems like kind of the same thing. Just as every man really needs at most, 2 watches (and can probably get by with 1 if he really had to), most cyclists need, at most, 2 bikes, and can probably get by with 1.