The money is typically relatively low maintenance on any subsequent playthrough, as it's the 2D art pieces that eat up the most.I don't try to max everything out, though I usually pump up the money so I don't have to mess around thinking too much.
Honestly, maxing out your Brawler stats quickly breaks the economy so much because once at max you can earn $2 from every free roam just from that, meaning once you get the second phone every free roam moment allows you to earn $4 within maybe three minutes.