As of 2020, Sitecore no longer provides any type of support for websites running any version of 7 or 6. In 2021, you may no more get security updates or assistance with manufacturing incidents for 8.0 and 8.1. In 2022, this kind of support ends for 8.2. What does that mean for you? In short, if you opt not to update, it implies that you are putting your website and your organization at a fairly precarious position. When you set off updating, it's only a matter of time until something breaks and your site goes down. If you are sitting on an unsupported version of Sitecore, then you may just end up the creek with no paddle.
Sitecore updates always require a fair amount of due diligence, planning, and attention to detail in execution. Unfortunately, speak to anyone who has completed a Sitecore update before (particularly one which skips intermediate releases) and they'll let you know the approach is often not as simple as it sounds. If you or your company have the budget I'd definitely advise employing somebody who has planned and executed an upgrade before, as experience may count for a great deal of time saved in preparation, efficacy, and debugging issues later on.
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