This is a modern list for the progressive thinker, with due respect to cycling heritage, of course. In no particular order, these are the bikes you need. The justification for each is self-evident (brands are in parentheses).
1. Full-carbon pimped out featherweight hillclimbing rig. This should not weigh more than 15 lbs. and should work out to roughly $500-$600/pound (Calfee, Parlee).
2. Titanium steed (Merlin, Moots, Serrotta, Seven). Ahhh…titanium.
3. Full-carbon or carbon/aluminum workhorse/daily driver. This bike has multiple personalities. It can also be known as your crit bike, rain bike, commuter, etc. It may have mismatched components and a few battle scars, but it’s the one you’d miss the most, as it’s probably the one you’ve had under you longest (Fuji, Giant, Felt, Jamis, Cannondale, TREK).
4. Old-school Italian steel. This bike should have been made at least pre-1990 to even be considered (Tomassini, Somec, Gios, Colnago, Ciocc, Masi, Merckx w/ Columbus tubing). Please, please dress it in appropriate-era components. For the love of Pete, don’t put Shimano 105 on your classic Pinarello.
5. Your ultra-exotic “because I have the money” showoff bike. Different from your hillclimbing rig, this is purely for eliciting lustful envy from your fellow clubmates. It weighs a couple of pounds more than your featherweight, but the same $/lb. factor applies (Kuota, Wilier-Triestina, Cyfac).
6. A fixie (Surly, Cinelli).
7. A full-suspension MTB (Turner).
8. A TT rig (Aegis, BH, Cervelo).
9. A beach cruiser (Electra).
10. A Skeppshult (look it up). Keep it at your cabin.
Now all you need is roughly $50,000 for this ultimate bicycle shopping list!