by Howard Miller.
You should never get yourself in a position where upgrading is a major hassle. That's how you end up using a several year old, unsupported release and - while I don't want to overstate the case - that should not be seen as good practice on the security and stability front.
I recommend making regular, small upgrades. You get used to doing it and any issues that do crop up are likely to be minor and easy to fix.