Should I update my Fedora 25 Workstation and if so how can I do it

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I agree that reinstalling would probably be the best option. If your home directory is in its own partition or LVM logical volume, you should be able to retain your home directories while reinstalling the OS on the boot and root partitions/volumes. I did this recently with a Fedora 29 system that I have been upgrading since Fedora 23 and I was losing confidence in the installation. During installation, I chose the custom partitioning option and basically instructed the installer to reformat the /boot and /root logical volumes and NOT to format the /home. I would backup /etc, just in case.

it's not safe to skip more than one version, but you could go 25-27, make sure it's working properly, then 27-29. If all goes well, it's easier than a complete reinstall, because you don't have to go back and install everything you'd had before. Just make sure to back up /home before each upgrade, even if it's on a separate partition, Just In Case.