1 - Two main reasons, story consistency and because it's better for the structure. I'm not sure where you are in the game yet, but many of the later story events are centered around "first times". And of course it doesn't make much sense to have that happen twice. The level end story events are particularly significant milestones story wise where this comes into play. Structure wise it's best for the content to just move onto the next stage once you finish one. For consistency, avoiding bugs and avoiding any clashes between new and old content (such as a system/mechanic working differently from one stage to the next). It just makes development a lot easier.
That's the motivation anyway. I rather underestimated how many people would choose to do the two paths at the same time. In fact it seems like basically everyone does. It's something I'll have to consider when designing any future characters, so you might find things work a bit differently when we get to those.
2 - I moved away from it because I got the impression most people didn't even find it. It's only available once per week at a specific time. It was a concern I had even before releasing it publicly, and specifically asked a tester of mine if they found it, which they didn't. Honestly you might be the first player to even mention it all. It doesn't really make sense as a daily thing, and would be way too much of a money sink if it was, so its caught in a hard place where people can't find it, but it can't be present much.
Obvious solution is to make it available in a different way, but I decided to just drop it instead. The story moved on from the money troubles between the pc getting a job and jen getting her new jobs. And any good ideas I had for content coming from the shortage event could easily just be done in the paying rent or reward point events.
Saying all this though, if you like the money stuff, you might like something that's coming in the next update
Thanks for taking the time to write so much feedback, I appreciate it! Hope you continue to enjoy the game.