'Do it all' bike: randonneur and dirt

I am going to get, at least, two of three new bikes I want when I return to Canada.  The bike I will get for certain is the one I'll use to commute: a fixed gear that can take fenders, and I may use the Sturmey S3X hub.  The bikes I may have to choose between are a randonneuring bike to replace the road bike I'll leave in Japan, or a fat-tire bike to ride off-road and through winter.  The choice will come down to the time of year I arrive, and if I can accept the stupidity of Ontario drivers while riding road, after several years of far better Japanese drivers.

If I get a road bike, I am going to do it right.  I want one that will not be heavy or sluggish, and fulfill the following, so I can randonneur, light-tour, and dirt-road it (and I can't afford too many bikes...):
- steel frame
- double crank, with low to med-high gearing
- room for 32 mm tires with fenders

- which means cantilever brakes

- indexed/friction switchable bar-con shifters, or Retroshift levers

- 32 spoke wheels

The easy way to get most of this stock is to buy a steel cyclocross bike; the harder way is to get it built up the way I want.  If I did, since I have a budget under $2K, this is what I'd do:

- Velo Orange Rando frame and fork*, without the racks and fussiness of the build in the picture**
- 30/46 crank (Phil Wood VBC or Velo Orange Grand Cru)
- narrowest bottom bracket possible for narrowest 'q-factor' or drive-side offset
- 12-28, 10-speed cassette (12, 13, 14, 15, 16, 17, 18, 20, 24, 28)
- canti-brakes
- bar-con shifters
- 32-spoke wheels
- long fenders (plastic is quieter than prettier steel)
- Brooks saddle: Swallor, B17N or B17N Imperial
- reliable workman components (Tiagra level) but some money in the wheels so not too heavy
- puncture resistant tires that are 'supple' and not too heavy with Kevlar bead

*A Soma Double Cross has 5mm to 10mm less BB drop than the VO Rando, Casseroll,or Steel Wool Rover, and I don't need the clearance...
**Revelate makes a bigger, better, more modern seat trunk; a handlebar bag off a Thorn Accessory bar is lighter, quieter and less fussy - or try the Revelate Handlebar system.