In terms of pure utility:
- A touring bike always set up with front and rear racks. For long distance load carrying (and touring, duh). Moving backwards on this one...selling my touring bike since I don't have the time to tour much.
- Xtracycle. Missoula where I live most of the year is flat so maybe I'd do a 1x9 or internal hub. Definitely 26 inch wheels.
- A rando/sport touring bike. Would be my main bike. The other motive is I'd love to do some rando riding eventually. This would be for light loads/commuting too. I think it would have caliper brakes, not cantis like the tourer.
- Ultra beater singlespeed. For those really nasty winter days.
Branching into purely recreational riding:
- Nice cyclocross bike. I'm quite happy with my current one, but titanium would be awesome.
- 29er mountain bike/moster cross with disc brakes and dirt drop bars. Steel or titanium.
- light aluminum hardtail mountain bike. Or maybe even a full squish.
- Carbon road race bike
n+1, as they say...