My organization has a lot of legacy ASP software on its hands.
Since our perception is that Microsoft has shown a distinct lack of support for its older products, we need to figure out what to migrate to next.
If we migrate to ASP.NET from Classic ASP, It feels like that'd be a 'complete rewrite' "migration". Since that is probably the case, we're thinking about turning to a free (as in beer and as in speech) platform. I particularly think our investment (in programming effort, I mean) would be better spent with a platform that will let us evolve, rather than forcing us to dump very single line of code every 4 / 5 years. This is the main argument we've been using to advocate moving towards a 'free' platform.
Currently we're thinking about using a mixture of Java with a dynamic language like JRuby or Groovy.
My questions are: What would be a good migration choice? Are our fears unfounded? Would we (conceivably) need to rewrite a large portion of the codebase after 4 or 5 years anyway? What arguments do you have for moving to either .NET or to a free platform?