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A friend asked that I help move his site from one host to another. Turns out it's a site within a CMS called N2CMS. I've never heard of this and it's been very problematic. I looked for info online and it looks like the CMS is old and barely/not supported.

Given that the site is small in page count and complexity, does it make sense to continue to try and get the N2CMS implementation up and running or just suggest another CMS?

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IMHO and what I do is migrate the site to one I am comfortable with and is a mature platform. For me it is DNN. Takes about 10 minutes to setup with templates and modules and then content migration can be easy and quick. Easy, as in i can reproduce the pages and design from the old site without any difficulty. Quick, if there are only a few pages the DNN template and layouts work so well.