playing eve with 1 monitor is just silly (i played on a laptop for over a year, will NEVER go back)
that said, I doubt you would get caught if you had dxnothing windows set up to show your shields on all your toons and had them set up to switch to the correct window on click. (ie: toon 4 is taking damage click to switch to toon 4 pop cyno, click through 1-8 to jump to toon 4) as you're just using it as a window management tool
I think they're going to crack down on the "perfected" 10 toons with overlays and guns on one screen (no proof, no rumor, just a hunch)