Hi!
As a native Russian speaker I can say transliteration like Ščedrin would
look very unusual for Russian-speaking person (assuming they have
experience at all with non-cyrillic transliterations, which most
internet users do). Something like Shchedrin looks more familiar and
seems to be much more common. While letters like ч and щ can indeed
generate some long combinations which are not very visually appealing, I
think it is more common than diacritics, which most people I think would
struggle with.

As for Hebrew, there are standard transliteration rules, which look a
bit weird since they are not phonetical but rather base on spelling and
distinguish some letters that all but lost their phonetical distinction
in modern Hebrew (such as kaf and kuf) - but they are frequently used
for signs, street names, maps, etc. These rules have been recently
updated but old ones still are used from time to time. See more at
https://en.wikipedia.org/wiki/Romanization_of_Hebrew