Well, I tried something similar. I have a 21" widescreen plus a 17 4:3 older LCD. RIght now I run main on big screen and 3-4x Alts on the 17". I got a hold of a 23" screen, which I quickly found was too big for one window (I have it positioned pretty close to my viewing position due to desk layout).
I thought, what if I scaled main window down and just stacked alts down the right side using ISBoxer's handy reconfig tool. Turns out, the windows were just too small.
For normal running around, it's fine I guess. But occasionally I need to click a quest item or portal using broadcast and need to make sure that everyone is oriented correctly. I just found the screens too small.
Now, a 27" might be ok, since you have more space, but I'd try it out somehow before you commit the $$.
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