You're not thinking of it long term. In the short term you might be better off deciding when to update yourself, but in the long term you will be infinitely worse off because the reality of business practice is to delay updates until something catastrophic happens just to save a few bucks in the IT department. This approach merely means your system will run smoother over short time scales, while it becomes a complete clusterfuck over long time scales.
True, but only rarely and with foreseeable and preventable damage. The alternative leaves you open to basically infinite losses at an exponentially increasing risk over time. That tradeoff is simply not worth it if you want your company to exist long term.
