It's not that his family has more money (or not entirely that) they're happier and more themselves.

George is the writer he always hid deep down inside, Loraine is happy and doesn't have the drinking problem she is strongly implied to have before, his sister isn't a lonely spinster just waiting for a man to show up and make her life better and Dave had a better job rather than working on fast food (not sure why he's still living at home and working on a Saturday but he certainly seems happier about his job and life).

To make it all about money misses the details.

Supernatural was always at its best when it kept effects minimal. A lot happens off camera and it benefits from that.

Think about the one time they actually showed an angel arriving in a scene as opposed to all the times they just showed up off camera and which is more effective.

Given that he was stated ti be a collage professor teaching Star Wars as a subject it was already weird that he wasn't free to return with Donna over the summer. Unless he also teaches classes on the summer for some reason.

The biggest issue with the Winchesters was setting it in an alternate reality. Whole it did grant them more freedom and eliminated the worry of breaking cannon it also never felt like Supernatural.

They changed a lot of established details and broke some of the shows taboos (such as having a lot of effects and a recurring monster that looked inhuman), making it feel too different from the parent series.

At this point I wish they would just do streaming movies instead of a series. That would give them more time and they could split a whole season's budget between four one and a half hour movies.