1. I strongly suggest atleast staying up to date with the latest release in whatever tree your in currently 3.6.12 I beleive at the very least, generally plugins, and templates will work just fine thru these changes though you may have to implement CSFR protection which is some simple search and replacing in templates.
2. If you dont' need the features that 3.7+ is currently offering, then honestly there isn't much need or reason to upgrade.
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