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Communicate, communicate, communicate letter is out.

Update!  Update now!

A new version of an operating system or tool you use is out.  Should you upgrade now, in a few weeks after reading through the forums, when version x.1 is out or wait until the next version with the feature(s) you really need is out?

The immediate answer is Now.  Other answers require an explanation; to not stay current with times requires a reason.

An upgrade of a system might require time, resources and risk.  For simplicity I use the word “cost” for these as a group.

Is this cost a problem?

Toy with the idea of updating something as big and complex as an operating system in small small pieces, say once a week, or even better: whenever available.  This is already done today with antivirus and patches.  Even though each and every update risks a cost they are applied all the time.  Besides, if one has business critical 24/7 systems one most probably also has checkpoints, backups and redundancy.
Alas: already today we are updating our systems continously without hesitation and it seems to work splendidly.

The job must be done anyway

As long as a system isn’t planned to be scrapped it has to be maintained so the update job has to be done anyway.  The cost is there – it is just a matter of paying the debt now or later.  While the debt isn’t payed someone else has to pay; either the very person who uses the OS or tool or the whole business unit.  By not upgrading one moves the cost from one place to another while still keeping the cost to be payed at a later time anyway.
If one waits until “next update” to do two updates at once one does just that.  Waits.  And then updates twice.  The cost is mainly dependant on the change in functionality – only partly on manual work.  Two updates directly after each other won’t decrease the cost; it will instead increase the amount of changes, the risk and the resulting cost even more.
If each update requires a lot of manual work one probably has yet a problem – the lack of dexterity to do something fast and simple.
Alas: Update now.  You will update anyway in a way or another.

What if the the update doesn’t contain anything needed?

Do the update anyway.  The situation is now such that any problems that arise is due to the update process only, not the functionality.  A golden opportunity to weed out problems with the update process.  By next update, the one with changed functionality will run smoother and with less cost.
Alas: Update now.  Take the cost now.

Child diseases

Everyone has them.  Both this update and next.  Make sure to get as few as possible.  Alas: update each time.  Now.

Dead time

If one spends a week on forums to find out if others got problems oneself might get, don’t wait with starting the process of updating.  As soon as the update is available, start working on it.  As soon as the update is verfied, apply it.  Remember: the update has to be done anyway and there is no reason to let the rest of the company pay for a week more with an old system.

Psychology

By choosing to not upgrade one also tells the surrounding that staying current with time isn’t proper.  As a business leader the signal is that work is done at desk, in chair, 8 hours a day with the tools in front, not with the tools available.  Progress? things others do.  As a IT pro running the computers one tells the users their time and working environment is less worth.  As a developer one is simply smoked.  A developer who doesn’t embrace change maybe should change line of business – conservation or royal court comes to mind.