I think one issue here is that the majority of tenants do not see entering in a work order online as a viable or quick resolution. If someone's toilet overflows at 3am, they need someone awake and responding right then if possible. To them, entering a request for plumbing repair seems like getting in line at the DMV, and to be honest, it would feel like that to me as well.

Not decrying a software solution, but while I pay almost every bill online, most of the tenants I've had just pay cash or check, and we have an online option.