Another thing is that even though both TLJ and TESB are the low points, try to compare the endings. TESB’s ending still seems more hopeful, even if only visually due to the room of the final scene being white and Luke and Leia wearing white, while looking at a beautiful space-y thing and awaiting for another adventure to save his friends.

One may argue that TLJ’s ending is even more hopeful due to the whole message that Luke was trying to pass on, and then broom boy showing the rebellion spreading, yadda yadda yadda, but in the end, for the characters it seems much more hopeless than TESB’s. Compare Luke’s last line spoken in TESB to Rey’s in TLJ.

“I’ll meet you at the rendezvous point in Tatooine. Chewie, I’ll be waiting for your signal. […]”
“How do we build a rebellion from this?”

Pay attention to their faces, to everything. Rey’s basically hopeless, holding a destroyed lightsaber in her hands, not knowing what to do. While Luke is hopeful, determined determined to rescue his friend, it’s under his control. And he’s fixing his hand, putting that behind him.

Obviously they’re different movies with different characters in different circumstances, but it’s just to show that you don’t have to apparently destroy all of the character’s “hopefulness” and will in order to put them in their low point.