>Not going to lie: I really enjoy having money to spend. I like the freedom to go out to eat, travel, shop, etc. If I quit, I can say bye-bye to that.

Do you like it more than making films? Seems like it, since that's what you're spending it on. Make a bunch of films, and don't move until you have a solid plan for developing a larger fulltime film project and understand the risks/opportunities.

It can be done. One of my co-workers made several shorts while working fulltime.