If I had to guess, most of your expenses are for the servers, so why not just outsource the hosting to the end user and let people host the webapp themselves? Maybe charge people a one time fee for software itself and offer free updates, then charge for premium version updates.
Regardless of what happens, you'll be making some money on just the code itself. Even if people decide to pirate the software, you'll still make some money on the premium version updates. This is better than a net loss just to run some DRM on the software.
Basically the same model that most open-source software startups use, the software itself is free, but the enterprise features, updates, and support are not.


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