Why can't Rhino fillet this object?

I’m sorry but I find your comment a bit disingenuous. Rhino WIP is being developed on many fronts, one of which is improvements to fillets, and another is the addition of puffy curves. While the latter may seem like a frivolous addition, it adds value by enabling users to do things they could not do before. A more comprehensive list of topics being worked on for the next version can be found here: Rhino WIP Features

As for the improvements to fillets, I’d like you to peruse the following topics and help us improve things by coming with clear examples of what is not working for you. And let’s be clear: it is easy to come up with a model that gives problems making fillets. The forum has many examples and we have many open tickets with these examples. This situation will not change in the next version of Rhino, but the claim that Rhino WIP doesn’t seem to handle fillets any better is not something I can agree with.