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(Menelaos:) "[….] no one of the Achaians labored as much as Odysseus labored and achieved, and for him the end was grief for him, and for me a sorrow that is never forgotten for his sake, how he is gone so long, and we knew nothing of whether he is alive or dead." (4.106-110)
Well, this is pretty grim: Odysseus suffering and labored harder than anyone else, and he doesn't even get a glorious death—just an embarrassing disappearance. Is it all worth it when he returns at the end?
(Penelope:) "Hear me, dear friends. The Olympian has given me sorrows beyond all others who were born and brought up together with me for first I lost a husband with the heart of a lion and who among the Danaans surpassed in all virtues, and great, whose fame goes wide through Hellas and midmost Argos; and now again the stormwinds have caught away my beloved son, without trace, from the halls, and I never heard when he left me. Hard-hearted, not one out of all of you then remembered to wake me out of my bed, though your minds knew all clearly, when he went out and away to board the hollow black ship. For if I had heard that he was considering this journey, then he would have had to stay, though hastening to his voyage, or he would have had to leave me dead in the halls." (4.722-735)
Talk about mom-guilt: Penelope actually says that, if she'd known Telemachos was going to head off on his road trip, she would have literally died. Is this an overreaction? Or is it honestly kind of justified—since without her son, she'd have no male protection?
By nights he would lie beside her, of necessity, in the hollow caerns, against his will, by one who was willing, but all the days he would sit upon the rocks, at the seaside, breaking his heart in tears and lamentation and sorrow as weeping tears he looked out over the barren water. (5.154-158)
Odysseus has everything he could possibly want with Kalypso: eternal youth, luxury, prosperity, and sex – but still, he yearns for the trials of mortal life.