This kind of thing is top of my list when I think about how little enthusiasm I have for taking our current on-premise, installed enterprise software, and trying to turn it into a SaaS. As a small company, we've barely got the horses to handle the much-lower levels of complexity involved in building and supporting a mostly monolithic application, where we can offload all of the ops and deployment and first-line support duties to our customer, once they've got it installed and running.

I just start checking out when the idea of creating a cloud-hosted, multi-tenant version of our product is raised. Scale, security, liability for data protection, 24/7 operations support, billing, and metrics for billing, all this stuff we don't currently worry much, if at all about, would become first-class concerns. Unfortunately some people seem to think you just wave your cloud wand at things, and poof! everything is magical.