WARNING: This post is lengthy, detailed, and individual. Only read if you have the patience and willingness to help me understand what's going on with my fitting.

Okay, here's the thing. I bought a Cross Check last fall. The LBS [Orange 20 in Hollywood] felt I was between a 58 and a 56. We ordered both and the 58 was way too big for me, so I bought the 56 which fit me okay. However, I've always felt a bit stretched out on it. I've done everything I can to make it smaller short of buying a new frame. I bought cross levers, so I could reach the brake levers in comfort and now I pretty much almost always ride the tops. I am able to reach the hoods but I just can't stay on them for very long due to the discomfort. I bought a 90mm adjustable stem to replace the stock 100mm stem, and I've been fitted by the LBS [a local suburban LBS] so all the adjustments have been made and everything is where it should be. I've mentioned to the LBS that I feel a little stretched out reaching for the hoods and they said it is more or less normal to usually ride on the tops. They rotated the drop bars to bring the hoods closer to me, but nothing. Still cannot ride on the hoods for any length of time. It seems like everything I've done has been band-aids on a more serious problem.

I need a smaller frame, it's the last and most expensive thing I can do to get a better fit. I am volunteering at the Bicycle Kitchen co-op that happens to be across the street from Orange 20, so I walked on over there and told them about my problem and they agreed that I may just need a smaller frame. I test rode the 54 CC and it felt great. Instead of riding default on the tops, I was able to ride the hoods the entire time; my neck felt less strained to look up even without the rise of the adjustable stem I'm running ATM, and I gained about a half inch of stand over height. I just liked it much better and that is the bottom line. I don't need affirmation. I know what I want.

What I don't understand is the math, why does the 54 feel better?

54cm [stock configuration]
eTT 560mm + stem 100mm = 660mm
56cm [current configuration]
eTT 570mm + stem 80mm = 650mm

Because the adjustable riser stem is shorter than the stock them, the current configuration on the 56cm is shorter than the stock configuration on the 54cm. It's shorter by a cm.

Alternatively, I can use the adjustable 90mm stem which when raised up completely shortens to 80mm. That would result in a reach of 640 to 650mm.
54cm [with the current smaller stem]
eTT 560mm + stem 90mm [80mm] = 650mm (640mm]