I read this last weekend and have been meaning to reply. On the specifics you described it's possible we just have incorrect data. In the general case though I agree with you. A couple of months back we scaled down our information density and modified how we pick labels because in a number of areas the map was too cluttered to read. This was particularly bad for the mid level zooms in Europe. The change probably went too far though because, as you pointed out, we're not surfacing enough information in more sparsely populated areas such as the midwest. This is on our radar of important things to fix, and I will sincerely try and find time to test out some ideas on improving it.

As for your feature request, right clicking in maps will give you a context menu with the options "From here..." and "To here...". I believe a similar feature was just recently added to the android client.

Thanks for the detailed post, I'll be sure to reference it to see how we improve.

I work on maps at Google and we do show toll road designations on freeway routes where we know of the restriction:
https://maps.google.com/?ll=47.635784,-122.250881&spn=0.082012,0.17458&t=m&z=13
https://maps.google.com/?ll=40.765917,-74.006052&spn=0.04609,0.08729&t=m&z=14

We start labeling toll roads at zoom 13, I think it would look too cluttered to label them in the more regional-view screenshot you posted. As for styling them differently, using a new color seems confusing without also adding a legend. A different road color could mean the highway is more/less prominent or (in some areas) a seasonal route. Directions has an option to avoid toll roads, which to me seems sufficient for regional driving. For tolls on bridges or narrow corridors where one may have many alternate route options available the roads are usually only visible at z >= 13 anyway.

Does this change your mind at all? :) Maybe we could address some of your other gripes?