Looks like the updates are going to become more frequent. All we can do is review the code a lot and that is not foolproof as there will always be bugs.
Is there a way to place a hold on those patches that require a reboot and perform them at a later time? I have seen companies change Linux distributions just for this ability.
If so, can the operator bail out and are they notified (in a way that they can point to after the fact) that a reboot is going to be required before they even begin the process? If they are notified and go ahead, they own it. If they can cancel the job and let their supervisor make the management decision to go ahead then it is not really their concern. Either way, they are covered.
If the only way of knowing if a reboot is required is to apply the update, the ‘old school’ approach might work. For those younger admins, it was to patch a tertiary set of servers and if that worked, move on to DR and then swap that set with production while the production set was patched; then swap back. Every set has to be in sync and the patches had to be applied in order. I have seen the tertiary set skipped for budgetary reasons but this was always considered suboptimal. This method is still followed in hypercritical 24/7 banking and government operations who can pay. That said it does catch the reboot problem before service is interrupted.
IMHO, it is far better to place the hold if we can.