i think you did better than I did -- my first versions failed to separate the shading at all; the second try with the pear was a little better but harder than it looks!

You got the right idea for value grouping and range distribution by the second drawing, so you're on the right track :) For the pear, the values are distributed within the shadow range--the value scale should be like the one you used for the portrait, with the lightest value being the blank page. This should also help simplify the groups into larger shapes with less focus on small details. As for the portrait, just watch out for the small areas of light at the bottom of his jaw and his shirt. While there is a change in value a bit lighter than the rest of the shadow, it's still part of the shadows and should appear darker than any value in the light range. Looking at it as a whole, the face seems to be skewing slightly darker than in the reference, as it appears that the majority of the area in light is grouped as the middle value, but try squinting at the image to see the larger groups--there's less of a sharp jump from the lightest value to the middle value, so try expanding the area with the 2nd lightest value. And as you pointed out the proportion issues, it's good that you have an eye for it already. Keep practicing, but don't worry too much about it--there's a lesson in the course later on dedicated to building the development of this skill. Good work overall, keep it up!