I think I've decided...(kind of long-ish)

[MartianDestiny]

Do I have performance oriented options in Steel or Aluminum? I know this sounds like a silly question - and feel free to give silly responses with some serious advice sprinkled in.

YES!

I think you could definitely find something in steel that would be a little more performance oriented geometry, still sit you more upright than a race bike, and maybe even have mounts for a basic rear rack (or not, since you already have the trek).

Custom is an option, though perhaps expensive (frames would start at $900 and go up up up from there).

Non-custom options off the top of my head would be bikes like:
Surly Pacer
Salsa Vaya (new, and actually a tourer)
Salsa Pistola (steel, road bike, century based, nice tall headtube (upright))
Salsa Casseroll Double (rack mounts and overall very versatile frame)
Gunnar Sport (again, long distance based with taller headtube)
Gunnar Roadie (more pure race)
Gunnar Fast Lane (roadie with disks, if that interests you)
Curtlo Custom Road (his customs start at $990 built the way you want them)
Jamis Quest (nice classic, old school road look and comes in WSD)
Jamis Satellite (comes in women's specific)

I think most of these would fit in with your style more or less and give you something a little different than your tourer in your stable to pick from (some more than others). I think you'd find a messenger bag fine with most (or all) of these as well as I tried to look for taller headtubes for a more upright geo than a TDF bike I didn't pay too much attention to overall geo, so I suspect these run the gammut from pretty close to a tourer to pretty close to a race bike.

Edit: if you wanted to go pure on roadie for something different you could look at a Cervelo RS. It's definitely a pure carbon race bike, but they've built in a taller headtube. It's definitely outside of what I'm picturing you on from your description, but it could be fun to take out for a spin if you could find one around you (Trek does a similar thing with their Madones with the performance and sport fits, one with a taller headtube and more relaxed geo, the other more racey. Not sure if this trickles down into the Aluminum road bikes in their line or not) Cannondale also makes an aluminum Synapse with a more comfort bent (but still fast), again, probably outside what you are really looking at, but could be fun to try out.