To your last point was Simple's cost of funding just too high?
Simple's funding likely only increased their runway while they were building a product that I'm guessing was net-negative. I don't feel like they could generate enough revenue to cover their burn rate using their holding bank strategy. If they could I suspect they would have continued down this path as a fearsome (future) competitor.
Once some bank builds the underlying technology in-house correctly they're going to be nigh untouchable.