Deciding whether to get the latest operating system depends largely on personal circumstances. The most up-to-date systems usually offer better features and increased security. The drawbacks are the cost and the potential compatibility and performance issues with older computers.
One major reason to have the latest operating system is for security. As a general rule, manufacturers improve security with each new edition. They are also less likely to prioritize finding fixes for security problems with outdated systems.
Support is another issue that can affect which edition of an operating system is best to use. Most manufacturers phase out support for older systems over time. That said, it is worth remembering that third-party support is sometimes available from independent companies after official support ends, though this can be expensive.
A reason to avoid getting the latest operating system is cost. It can be expensive to upgrade computers, particularly across a company network, and this expense may seem too much if the current system is working well. Of course, this is not an issue with open source operating systems such as those based on Linux.
The other major reason not to get the latest operating system is hardware and software compatibility. In some cases, a new system won't work with all the devices or applications you currently use, though sometimes it can be possible to use a technique called virtualization to run older applications in the new system. The new system may also demand more computing resources such as processor speed and memory, meaning performance may suffer on older machines. Windows 7 was the first version of Windows in many years that didn't have significantly higher resource demands than its predecessor.
While operating systems are frequently updated over the Internet, Microsoft uses a service pack system. This means that at regular intervals, usually around once a year or so, it issues a major update that brings together all the software and security updates since the last service pack, or since the system's release if it doesn't yet have a service pack. At one time this served mainly to help people who didn't use automatic updates, such as those on dial-up connections, to catch up. Today, the main purpose is as a practical method of making sure that new computers sold in stores are relatively up to date with the latest operating system edition. It's not practical to repeatedly update computers waiting in warehouses, but new machines can be built with the latest service pack in place.
Some users, particularly in the business sector, believe it is good practice to wait until the first service pack is in place before getting the latest operating system. The theory is that this allows time for most major bugs and problems to be ironed out. Microsoft argues that this is no longer relevant, given that new editions of Windows now go through public testing that catches most problems before the new edition is released.