I think you're looking at it wrong... 1.102 to 1.093 isn't 22 points - it's only 9.
And if you don't trust Beersmith, the simple formula C1V1 = C2V2 backs that up:
102 X 5.0 = C2 X 5.5
C2 = 102 (5.0/5.5)
C2 = 102 X 0.91
C2 = 93
I think you're right.
I brewed this today. With my rig I got the 1090 OG, but I had to do a 90 minute boil and ended up with 4.8G into the fermenter. Not too bad. Also ended up subbing Wilamette for Mt. Hood as that's what I had on hand.
Forgot to add the chocolate during the boil too. I don't like to run chocolate through my plate chiller, so with the last beer I used chocoate in, I pumped hot wort into a pitcher with the chocolate in it and let it melt. Ended up just nuking the chocolate and pouring it into the fermenter. We'll see how that goes.
Otherwise, a successful brew day. This is without question the biggest beer I've managed to make. Hopefully my starter + one package of liquid yeast is enough. 2.5 hours later I have airlock activity, so I think I'm in good shape!