I got the Krag out and shot a few rounds today.  I had a few rounds of factory Winchester 180 gr ammo that I shot first and then some of the handloads described above.  I'm happy to report they are much lighter on the shoulder than the factory loads.

Accuracy would be hard to measure at this point, I was shooting offhand at 50 yards as this was more of a function test than anything else but I got all rounds on the target (really all I was concerned about right now). and grouped smaller with the handloads than the factory load. 

I shot out the factory ammo to clear some brass for some new handloads.  I think I will use 37 gr of the IMR3031 again, but make my COL longer, I'm thinking 2.95 since the 2.825 fed just fine.

Next step will be to shoot it from a bench and see how it really groups.