For what it's worth, here's my 2 cents: I think the concern that web2py is a one-man framework and how the makes enterprises (big guys) adopt web2py is a valid concern. Although in theory, people can simply fork web2py when Massimo no longer commits to the project, for whichever reason, from a bystander's point of view, it doesn't seem that easy. I am not talking about a legal perspective, I am talking about the meat of the matter. When I look at web2py's project on Google, there are a dozen developers. And most of the fixes are done by Massimo. And I maybe wrong, but I don't think web2py has a #2 guy yet (in terms of intimate technical know-how or time commitment). So the question: who can take over web2py, if Massimo no longer commits to it for whatever reason? It is not clear. So I think this concern is legit.
At the same time, I think forming legal entities might not effectively address this concern. It might even hurt it with much legal and administrative overhead. Drupal did not form any legal entity until it was really established with hundreds of developers and thousands modules. I think the real concern is that we need #2, #3, etc. guys, who know web2py as much as Massimo. I don't have an answer to this, but I think one way has to do with documentation, or rather a platform that assists developers to really understand the inner workings of web2py to make it really natural for them contribute when something goes wrong. Drawing a lesson from Drupal, it has a beatiful API documentation system, a beautiful bug reporting mechanism. And it is a magnitude more complex than web2py. In summary, I think one way to address this concern is establish a platform so that it really helps developers learn about the inner workings of web2py, fix and report bugs, etc.
