"Or am I just splitting hairs here? Maybe someone with more knowledge of frame geometry can educate me - do these differences make any real, well, difference?"
Those are real differences, how much they will be picked up on in blind tests is another mater, but all road geometry is pretty standard, so a 1.5 cm difference in CS length is big, unless one wanders off into bikes with extra long stays in the 60s. The problem with the Surly is that the smaller sizes are probably a better design. Being consistent in CS length is marketing.
"What really got me was the list of charitable organizations they support."
Very admirable, but for 1100 dollars in savings you could "do a lot of good" on your own.
The only problem I have with the Riv bikes is that you can buy a lot better bikes for 1500-2500. For 2500 you can get a custom frame from the best in the business. It's a personal mater whether you want to deal direct with a builder, or through an outfit like Riv. At the very least, those prices open up the whole universe of bikes. On the other hand, 400 dollars gets you a lot of frame but it isn't custom and it doesn't have the quality control one should expect from a hand made frame.