OK. So here's a combination that pretty much works: Deore FC 590. Old Exage 500 LX (48T), Old Sora 3x8.
Just barely. The outer chainring is a little out of true, which makes things interesting, but I just got it to shift on the stand. I think my embarassing commuter vs roadie shifter fail on Friday's commute was due to cable stretch on my new build.
Anyway, I think it's shifting well enough for a commuter at least.
It was my first time building up any bike with STI brake/shifters. So if this novice can get it to work, it should be doable. I think it just needs to be tuned a bit more finely.
I am considering finding a thinner 10 speed outer chainring-- the narrower width might make a slight difference in terms of making the whole thing narrower, even though it would wear out more quickly.