In general, the bulk of cash will be found on the Paths; you make more money slaughtering innocent-ish monsters than you do bartending.
(And no, there isn't "an order to follow" in terms of unlocking the Kings Dragon, despite the walkthrough having a preferred way. All content is available regardless of the first choice)
Thanks for all the help you guys.
I spent too much time on the paths just doing Treasures and Shrines trying to collect ingredients for Chloe.
Was trying to get to 50 and get a lvl9 pure damage gem.
Eventually I just gave them away as she wouldn't offer to buy them anymore.
Didn't get enough saved early as I sold her quite a few before I started saving them up.
Just noticed after doing a few runs on the path and killing stuff I now have over 5K so I don't need to cheat quite yet.
Of course I couldn't do the paths in the evenings so the bar was only option for making money in those time slots.
Probably also spent too much time reading and leveling up skills.
Day 124: Lvl 29, STR 45, INT 42, CHR 43, Swords 27
(Don't know if it's good enough yet, lol)