Do I (dare) upgrade iWork? Numbers? Pages? ???

[JamesD]

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On my iMac running Sierra 10.12.6

I have iWork '09
which gives me:
- Numbers ver. 2.3
- Pages ver. 4.3

It was my launching out on a big spreadsheet project that got me to thinking... hmmm...?

iWork is up to 2018
which has:
- Numbers 5.0
- Pages 7.0

I wonder if I ought to take this opportunity to upgrade iWork/Numbers/Pages (everhow that goes)?

Both of my old versions of Numbers and Pages serve me quite well.
I don't NEED to upgrade (to get new "features") from my point of view.

I just wonder sometimes about all sorts of this and that software,
if it's wise to fall too far behind,
where you might (?) get into compatibility issues? functional obsolescence? whatever?

The other side of the coin is, if I DO upgrade, how much trouble am I asking for?

Will my old documents and spreadsheets still look the same?
work the same?
STILL OPEN!?!?!?!

One post I saw... at the Apple Store I think...
person said the 2018 auto updates have #$@#'d Numbers up.
He now has to go to "the cloud" to open files or create new files.

I don't know what that particular issue is about.

But my point is, YEP, all sorts of stuff seems to be possible when you do upgrades.

So, all of this said, the pros and the cons, anybody got any comments, opinions, advice?

Roll the dice?
Or let sleeping dogs lie?

Don't know if there is one perfect solution (these days), but I am always interested in opinions and comments from people who have done something many times before.

Thanks,

James

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[honestone]

The usual approach is "If it ain't broke, don't fix it". But for computer software, that is not always a wise choice. One of the biggest risks with remaining with older software is the lack of security updates. That is especially true for the Mac OS. Sierra is a "somewhat" recent Mac OS, and I suspect Apple will continue to provide Security Updates for it, but not sure how long.

As it is, you are now two versions behind with the Mac OS. High Sierra came out a year ago, and just recently, Mojave arrived. If you either have a spare external drive, or room on an external drive, you could install Mojave there and test copies of your files there with the newer versions of Numbers and Pages. Of course it's important to realize that only the initial version of Mojave has been released. There are (most likely) some bugs in that initial release, and that Apple will undoubtedly be releasing updates soon. Typically, the ".1" update comes out about a month after the initial release, and the ".2" update comes out in November.

You might want to read the following threads here about Mojave:

https://www.mac-help.com/threads/mojave-ok.225041/

https://www.mac-help.com/threads/any-mojave-issues-thus-far.225026/

https://www.mac-help.com/threads/upgrading-to-mojave-os-10-14-might-be-best-to-wait.225013/

Also, you should try and follow any other threads (or updates to existing threads) here about Mojave.

Finally, if you do decide to upgrade, you would be wise to do a fresh, clean, "virgin" installation of the Mac OS you want to get to (High Sierra or Mojave, in your case). However, it is just as important that 1) you perform disk cleanup/maintenance/repairs, from a software perspective, on a frequent basis, and 2) you are making backups to an external device, again frequently.

With proper preparations (and doing the 2 things I just mentioned), the "upgrade" to Mojave will not be that stress full. Of course that depends somewhat on what software you are using for your backups. Most folks around here use Time Machine, which is OK, but I (and some others) use either SuperDuper! (that is what I use) or Carbon Copy Cloner. Either of those excellent products make a bootable backup/clone of your system. That's right, I said bootable. It's almost like having another machine, and definitely makes the clean installation of the Mac OS (and subsequent "migration"/copying of needed "stuff" from such a backup) much easier.