@ Username
“1. People who really grasped the holiness of a Sukkah – and these were Tzaddikim who’s sleep was a different sleep (for example, Shivchei Ari says how the Arizal would learn deep Sisrei Torah while he slept), so for them there was no problem sleeping in a Sukkah, so they had the Chiyuv DeOraisa to sleep in a Sukkah.
2. The regular folk, who didn’t know the Sisrei Torah behind the Sukkah. So they obviously didn’t feel bad about sleeping in a Sukkah, so they had the Chiyuv DeOriasa to sleep in the Sukkah.
It’s just that due to Yeridas Hadoros on one hand, and the spread of Chassidus on the other (so that even relatively simple people have some understanding of what holiness a Sukkah has), that there’s this guilty feeling.”
Did you ever learn the sicha inside? A guilty feeling due to [mis]understanding sisrai Torah has nothing to do with it.