Bryan, sometimes starting over fresh can be advantageous - kinda like "spring cleaning".  ;-)  However, theoretically "doing upgrades right" involves "spring cleaning" as well along the way.  This "spring cleaning" can involve things like:

• Removal of Telerik (9.8.0+)
• Removal of unused non-core extensions (sometimes this has to be a manual process when best practices were not used during development)
• Cleanup of web.config (often by doing a comparison between current and that from a clean DNN Install package of the same version - this is a sensitive area though so be careful and always make backups before changes)
• Review of release notes to make sure there is an understanding of any fundamental changes that could impact your implementation.

This list is by no means exhaustive, but intended to help think about some of the things involved.  Lastly, you can also leverage one of the trusted vendors in the DNN Community to help with the process.  Our team performs upgrades all of the time and no two seem to ever be exactly the same.  ;-)

In my experience, as long as you practice good "hygiene" in maintaining the site and its resources, upgrading should be the way to go. 

The only times I've recommended starting from a clean slate is when the website has been poorly maintained over the years and/or the number of core code changes are simply too complicated/plentiful to resolve.  

As long as no problems arise, and good practices are followed, nothing wrong with upgrading forever. I have multiple sites that started on v6 and on that started in v4 and are maintained up to the latest version.

Starting over on a site that is less than well-maintained involves a level of effort that varies greatly depending on the content. I did start fresh some small sites but for large ones, I try to upgrade as much as possible.

I obviously agree with Daniel, and I have a few sites that started on DNN 3.xx and 4.xx.  Also, one of our larger clients has between 1-3 sites per state that we recently upgraded from 4.xx.  So, it's possible. 💪🏽 

As long as you keep up with upgrades and keep things tidy, you should be good-to-go.  🥳 

Bryan, keep an eye on all the 3rd party modules your website uses as well. You may want to double check dependencies from the current installed modules before running upgrades (just to have a clear path of what modules you need to upgrade right after you upgrade DNN).

Also, I try to keep an eye in the SEO footprint (in the scenario you are going to start with a fresh install) you don't want to miss an important URL that is generating organic traffic (this might be another reason to keep pushing updates on DNN as much as possible). 

Thanks for all the input. Good stuff. Now, I simply have to decide on how good have we been at doing upgrades the "right way" in the past ;-)

Posted By Bryan Lynn on 2/20/2024 8:36 AM
Thanks for all the input. Good stuff. Now, I simply have to decide on how good have we been at doing upgrades the "right way" in the past ;-)

Well, if you uncover more questions, you know where to find us.  😊