> I can’t tell you why I keep returning to this venture when I’ve failed at it so many times.

Sorry if this sounds stupid or obvious, but with this kind of thing I find that it's easier to cross the finish line if you maintain humble goals. Focus on just getting a working end-to-end MVP. Refine and enhance it down the road; don't get stuck trying to make version 0 an awesomely praiseworthy effort.