My read was that it might also be the only way he can conceive of having a family. He certainly couldn't be married to a man. Not sure about adoption for gay men/couples in the 80's.
I don't know if it was just the one time (that's a wild amount of prize money) but yeah, Cherry did say something in the drag ball episode about feeling free of her gambling debt. This season has been weird about introducing heavy topics like Cherry's gambling addiction and Tamme's substance abuse to deal with her pain and then dropping them super easily.
I kept expecting his screenplay to come back but it seems he's recognized that hers is better and is fully putting his aside. Maybe he should stop trying to do autobiographical material. First Mothers and Lovers, now Paterfamilias.
I feel like in the context of this show we as the audience were supposed to understand that it was all or nothing. To Ruth, she saw the directing she was doing on the TV show as just for fun or to step in and keep this show going where she gets to act in some way. But she's no longer as desperate. She doesn't want to just kind of act as Zoya. She wants to be recognized as an actress. And here is Debbie framing it as an off ramp where Ruth will never again go in for an audition and maybe this time be chosen (insert reference to La La Land here). In the context of this show, Debbie is asking her to give up on that dream. I will note that even if you're doing Chekhov or All About Eve or whatever, being a stage actress means doing the same thing night after night, hopefully for months, possibly for a year or more. I'm not confident that Ruth wouldn't get bored of that the way she got bored of doing Glow. Basically, I feel like we've gotten away from season 1 Ruth who just wanted to act. I think she wants different things now even if she fully hasn't admitted it to herself. Validation, stardom, I don't know. But she's not the same as in season 1.