If it is decided that our system needs an overhaul, what is the best way to go about it?
Don't try and go 2.0 ( more features then currently exists or scheduled) instead build your new platform with the intent of resolving the current issues with the code base (maintainability/speed/wtf) and go from there.
We are mainting a web application that is built on Classic ASP using VBScript as the primary language. We are in agreement that our backend (framework if you will) is out dated and doesn't provide us with the proper tools to move forward in a quick manner. We have pretty much embraced the current webMVC pattern that is all over the place, and cannot do it, in a reasonable manner, with the current technology. The big missing features are proper dispatching and templating with inheritance, amongst others.
Currently there are two paths being discussed:

Port the existing application to Classic ASP using JScript, which will allow us to hopefully go from there to .NET MSJscript without too much trouble, and eventually end up on the .NET platform (preferably the MVC stuff will be done by then, ASP.NET isn't much better than were we are on now, in our opinions). This has been argued as the safer path with less risk than the next option, albeit it might take slightly longer.
Completely rewrite the application using some other technology, right now the leader of the pack is Python WSGI with a custom framework, ORM, and a good templating solution. There is wiggle room here for even django and other pre-built solutions. This method would hopefully be the quickest solution, as we would probably run a beta beside the actual product, but it does have the potential for a big waste of time if we can't/don't get it right.

This does not mean that our logic is gone, as what we have built over the years is fairly stable, as noted just difficult to deal with. It is built on SQL Server 2005 with heavy use of stored procedures and published on IIS 6, just for a little more background.
Now, the question. Has anyone taken either of the two paths above? If so, was it successful, how could it have been better, etc. We aren't looking to deviate much from doing one of those two things, but some suggestions or other solutions would potentially be helpful.