I would say you are better off, going with something proven to handle scaling, like mod_mono on apache if you are looking for alternative servers.
The integrated pipeline, routing, compression and caching features of iis are hard to replicate. But the app pool and failure rapid response stuff is hard to do without knowledge of the OS and the network stack at a root level.
Cassini doesn't claim to be multi threaded or handle any of the advanced e-tags or other header control issues that can be issues with iis, but are also usually set at sensible defaults in later versions of iis.
For the sake of completeness, you could do the older rails-mongrels model, spin up say 10 cassini's on ports 10100 - 10110, then use ngenx or apache to load ballance requests on those threads, and using a monitoring tool to redo requests to new threads when old ones go out to lunch and constantly be restarting 2 or so ports, because you get overloaded.