Those are a LOT of questions.

And some aren't even questions, more like suggestions?
So, I'll do my best here. Sorry if I don't cover everything.
Pregnancy: you will get pregnant if you aren't careful, but the main story won't be changed to adapt to a pregnant Jenny. More often than not, it'll mean you'll get an ending if you go through with it.
In the far future, I may include some limited content catered to the prego fetish, but it'll feel more like a DLC than integrated into the main game cycle.
Non-con (Mr. Humper sleep sex): I can't do that as long as I get 25% of my income from Patreon.
SubscribeStar has a much laxer content policy but they only work with credit cards, so a lot of people turn to Patreon to support via PayPal and Stripe, who are the actual Internet censors behind the scenes.
Don't get me wrong: I'd love to add more fringe content, but this is not a hobby. I'm feeding my family with this project.
If, in the future, SubscribeStar's income stabilizes well over the survival line, then I could risk losing Patreon's share and have that creative freedom.
Getting her bag back: Yes, she'll be able to.
New Game+: That's SO far into the future that I don't want to think about it. But yeah, I guess it would be nice. Noted.
And... sorry for ignoring the rest.