I have to agree with Lars.

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Cheers from Germany,
Sebastian Leupold

   

Speed up your DNN Websites with TurboDNN

First test it out in lab setting (by preference on a recent backup of your real installation). By the time the next version arrives, you may have an idea of how it will work in live situation. If you have real issues, skip the upgrade and wait for the next one. Don't forget to report the issue. Follow the upgrade forum and check if the issues affect you before you make your decision to upgrade. Never hurry.

The critical updates available sign, let it show for a couple of months. By the time DNN starts a new major version, settle for the highest minor version in the series.

I think that is the soundest policy to survive.

I recognize I took the wrong decision when I moved to 5.1. I have a site I can do that with, but for a university portal, I should have ignored the critical update warning. Only the superuser account notices it anyway and you can turn it off in the host settings of the live portal.

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The one-eyed in the land of the blind.

 
4.9.5 or 5.6.1. Everything inbetween has a critical security issue. If possible, stay with 4.9.5, but some extensions may force you to use the 5.x series.