How does the Scale lineweight check box work?

I've pretty much read every other thread there is about lineweight scaling, but I'm none the wiser. My drawing looks great with a viewport scale of 1:50, but if I change it to 1:500 it looks like a child went wild with super thick crayons! I always thought the "Scale lineweights" check box was there to deal with this, but apparently I'm not using it right.

I read in another thread that each paper size should have it's own .ctb with an appropriate lineweight. But what's the point of the "Scale lineweights" box then? Also it sounds very inconvenient as I use an array of sizes...

Hopefully I'll finish this day a much wiser man

I use the "Scale Lineweights" Box when i need to Print the Layout (usually 24x36) sheet half size or 11x17 (for reviews). I always use it in combination with the "SCALE to Fit" box or the "Scale: 1:2" thing.

That way the Lineweights dont go crazy when i print in a different sheet size.

And I wouldnt say every Papersize should have its own .ctb but every Scale u usually use should have its own .ctb File.

Hope this helped