Staggered or not?

How do you figure that??? If the overall diameter is "pretty close", then the sidewalls will also be "pretty close" if the tires in question are on the same diameter wheel.
A 27" tall tire on a 18" wheel has the same sidewall no matter what the width is. (example: 325/35-18 and 255/45-18 are only .08" different in overall height.
The tires in question: 255/45-18 and the 285/40-18 are nearly identical in height!
255x.45=114.75 mm sidewall (width x aspect ratio in %=sidewall height)
285x.40=114 mm sidewall
Divide those results by 25 (mm to inch).
That result is the .03" difference in sidewall height, but that is just 1/2 of the overall sidewall height.
So now to figure out the overall height of the tire: (sidewall height x 2)+ wheel diameter.
(4.5x2)+18=9+18=27" tall

Wind-Farmer was saying that the overall diameter of the tire and wheel is going to be the same with these sizes regardless of the wheel size being 18" or 20". However the side wall is going to be smaller or smaller on each since you've got more wheel and less tire.
 
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Old pic, since car has not been driven on the street for over a year. No longer street legal.

MVC-002S-6.jpg
 
Back rim looks a bit wide for that tire

Yes...they did stick out just a tad...maybe 1/2 inch. They were M&H Racemaster DRs 325/45/17. The rear rims were 17s deep dish 10.5.

Even back then, car had very little street use, 10-15 miles per week in 25-35 speed zones, so it was OK using the M&H DRs, even on wet roads. They are a very sticky tire, much better than Nittos and the car was running low 11s with them on a smaller turbo at that time. But the stickier the tire, the less efficient at evacuating water. Would not recommend for a true all-weather highway-speed daily driver.

Doesn't count coz not a street application, but here's a staggered look from last year's race season> Pic taken summer 2008... engine blew up around November 08.

FFW052508aa.jpg