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Care to share some of the challenges?
We’re about to do the exact same thing… going from 5 to 7 (hopefully).
We had some problems. We started on Friday (we actually outsourced the job to a local company). We encountered some problems with the installation and so things were not functioning properly till midway through Saturday. Overall it works and I like the software better. I would certainly recommend a complete backup prior to the upgrade.
I would suggest researching a server management company to do the upgrade. We chose a local vendor but http://www.4psa.com/ looks interesting, too.
Our SSL certs appear to need to be reinstalled.
We also had some problems getting Smarty back up and running (a template engine), which we’re still working through.