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Currently Microsoft offers two versions of Office. One version is Office 2019 which you can buy once a keep for lifetime, this is great option if you wish to save money and only want to buy software once, for a single computer and no tablets or smartphones, without requiring any immediate upgrades or cloud storage online. If you wish to get the latest upgrades all the time, install it on multiple computers, as well as across device platforms and need cloud storage, we recommend for you to consider an Office 365 subscription. You can find more information here.
Yes, most of the features of office require a properly registered account with Microsoft. This also makes it easier to store license information as once your license for Office has been activated it is tied to your account.
When subscribing to Office 365 you will always get the latest version of Office. So for example if you have Office 2016 you can easily get Office 2019 through your subscription and all future editions as long as you stay subscribed. You can find more information here.