It is in that the rasp pi's price doesn't have much slack. So it will never really go on sale whereas most other hardware with a few exceptions has a lot of slack. So it seems fair to compare the projected prices of things.
So, one party by default overcharging for their product and the other supplying it at cost makes you feel that when the one party puts their product on sale, a temporary condition at best the product suddenly become equivalent?
Then you should also compare the Chrombooks with second hand large format laptops, old servers on sale with new ones and so on.
Chromebooks 'on sale' are an entirely different class of product than raspberry pi's, they are larger, need wall power, have built in batteries and screens, are in general still more expensive and do not have GPIO.
I'm not singling out chromebooks. I'm just saying at $100 price point is crowded with a lot of old and new hardware. So a raspi may not be the best thing for you at that price point.