So with the current 68 Ω series resistor, I tried the two newer LED options. With the higher power surface mount emitter and the light pipe, the range improved from about 5 to perhaps 8 feet, but with the through-hole emitter, I got pretty reliable reception at 25 feet. I feel like reducing the series resistance down to 20 Ω will make the whole thing reliable at up to 30 feet, which I think will be good enough to score.
I'll try next when the v1.1 boards show up with the through-hole pads. I think, at least from an electrical perspective, that that's going to be the final design. Aesthetically, I am not sure, but we have at least 8 months to ponder that one.