Ok I need some thoughts on the following. For a client, we need to
redesign their website. The back-end was coded a couple of years ago
in classic ASP. It's fairly complex, with a webshop, uploading and
parsing of excel files with new collections of clothing, and stuff
like that. It took people about six months to build it back then.

Personally, I think now is the moment to also revamp the back-end, but
I'm having trouble to explain the reasons to non-tech people (bosses
and the client). I reckon I could build most of the back-end within a
week or two in Django. The problem is that neither the client nor the
boss care about the technology, as long as it works. They will not pay
for an upgrade of the back-end to newer technology, unless I can back
up this decision with valid points. So why should they switch to
something like Django? I can come up with technological points, such
as maintainability (less LoC), speed of development in the future...

Thanks
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