From playing v0.8.7 I have similar thoughts now to
AcTePuKc and I think actually an first step simple fix is to lock off areas more strictly until you progress to points where they can be unlocked. As I forgot how good the Bar job is that you should honestly just get that first rather than the cafe as you can get the tent within 2 days if lucky and avoid the apartment completely and the cafe. Although the bar quickly becomes useless and a chore if you can do the massage job since it only has one promotion with no extra way to get cash.
BUT
You can just skip to the city now and due to there being a lot of places to go and do stuff, you end up missing a lot of things relating to the story or progression of your character with exception to the bank opening up investments and saving cash. So I would honestly lock off the City saying the bus service is down currently or something so the player just has this small area to mess around in until roughly 20 in-game days pass or when the player needs to go there for truama (
as that's when you should be at the point to talk to the PI and expected to have 2k saved up for it) additionally I would also suggest that when the city does open up, make it so time doesn't pass anymore when you travel to uptown or downtown as it doesn't for the bus to the city and the player is used to the area now so can get around a bit faster if they aren't taking the bus to those areas too. I also feel that the game is close to needing a guide for various people/places for how to progress since the Library is pretty much invisible now and useless to go to since it's job to begin with is the same as the cafe in terms of pay.
I would extend this locking off of areas to the train-station too since at the start of the game only the farm is useful via getting groceries basically. This also means that Silvergate can have a bit of a boost since I noticed that from scavenging trash all day nearly I only got $20 worth from it so there's no reason at all to do it again presuming that there's something linked to do it like finding Dave's item eventually.
One final thing is that I don't know if v0.8.7 is just unstable but when I last played (which was v0.7 as a reminder) there was no errors nor missing or incorrectly named images....now I'm finding them with anything added since I last played and have found no further development done to any areas I could access. (as of reaching the mansion) Which leaves me still confused as to the possible purpose/benefits of doing various things like donating food to the charity and the farm. Instead it feels like areas that were barren becuase they were maybe just implmented have been left barren rather than fleshed out more like other areas were or the same detailing to them. (As the ATM and the Mansion's hidden computer interfaces are still the most cool things currently in my view)