I am slowly working my way through all the quests and bug fixing things now.. its taking alot longer as I go as I am spotting little things like spelling or quality of life things.. and fixing them also.
I have fixed the sister smoking one now.. there was an issue with the end repeating.
Regarding the money.. as the game develops you will find more ways to make money... (as in real life)
There is also another thing you can do to make money from the start of the game is selling your sisters underwear to arnold .. if you sleep they reappear once sold.. so thats a daily task.. also if you have finished the upskirtking quest, it becomes a paid repeatable quest.. The most recent quest when finished in one of the paths is going to become a weekly repeatable paid quest also..
There is also working for misty which is paid..
In the future I have a few other ideas that are going to be money generating also..
But I want it to be that you can really do everything each week (like in real life).. so you have to decide which paths you want to take in a play through