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    And watch the PHP versions. As you upgrade, newer...

    And watch the PHP versions. As you upgrade, newer versions ( and the corresponding plug ins that upgrade) will be looking for newer versions of PHP. There's no rule on how far back things are...
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    It's been a while since I updated a WordPress...

    It's been a while since I updated a WordPress install that was 2 years out of date. At the time I would only go ahead 2 versions at a time or you would run into issues.

    So yes, there are possible...
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