Vogol's Art

I think it would help to break this down by universes:

Regiment 803: Jill has a hard time sleeping alone because she feels isolated from everyone else. While she doesn’t exactly have an endearing personality that would attract people to her, she still gets incredibly lonely while she sleeps.

Mama Oxton also has some issues sleeping alone because she’s so used to having her wife next to her(which whom divorced her a few years ago). She sometimes will ask Alisa to cuddle with her after she switches Alisa off for the day just to keep Mama Oxton company.

Steven Universe AU:

If there’s anyone who has trouble sleeping here, it’s Amethyst. She only sleeps alone because she is rude and horny around people.

Aensland Estate: Mila has a hard time sleeping because she wants to have Rin all to herself despite Rin intentionally keeping distance from Mila. Talim lives alone and cakes her face in makeup in hopes that a husband or wife would come to her by bedside. Talim had dreams of having the lover of her fantasies and take her hand forever.

Pocket Mums: Dawn because of any identical reason to Mama Oxton. Not having her husband around anymore makes her antsy and uneasy. She misses having him there to put his arm around her.

Batman AU and JPWF: Perhaps Pam would be the only one who has a problem with sleep? But he’s not one to worry too much about sleeping, if anything he’d go down the hall and cuddle with his “stepmom” Ms. Quinn. Obviously in a non intimate way.