Always updating … 
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Once a day, whether it’s needed or not! 
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Before reboot or shutdown - sometimes twice per day and sometimes once every month 
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I might have mentioned it before (no kidding) - but I have constant (conky-driven) info on the count of updates, and their names - so I update when the counts grows a bit, and/or when I spot something I want updated, and/or when I want something to distract for a moment or two while ‘thinking’. All good reasons, right? 
Edit: I should also mention that this applies to my ‘main’ system - differing strategies are in use elsewhere, because the updates aren’t quite as ‘knowable’ where I am not logged in! Could be a week or more between checking out other builds, could be longer on another machine - or could be weekly but a week behind such as on my mirror server (I serve EndeavourOS and chaotic-aur on an EnOS build). Just about ALL methods of deciding work fine the majority of the time - with even LONG pauses being viable with some caveats (such as perhaps needing a keyring update, or needing to be ‘step-updated’ in smaller increments).
Basically YOUR way is the RIGHT way
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On my machine I use every day, I update it mostly once a day. On my laptop, however, I update on average every week.
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I update everyday, twice a day. I have other drives with this OS installed as backups (in particular another ssd drive) and if you wait long enough there have been times where I’ve seen over 500 updates in a single instance. Crazy? No this is what I’ve seen. The only risk you encounter is getting a partial or corrupted file on your system during the download or an out of date gpg signature on a file from some maintainer from out of date signature sources. So far the system has worked well for me. I also always burn the latest ISO file on DVD and thumb drive for reassurance that if my system totally crashes I can get it re-installed. Maybe not the best advice but this is what I do.
Rich
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I’ve been at both extremes. I update between several times a day and once in 6 months.
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Desktop (main usage) once a day. Laptop usually once a week. If I leave it for say, a month or two then I may have more pacnew files to deal with. If you leave it for a long time I would recommend updating your mirrorlist first otherwise things can get a bit messy!
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I run updates when I think about it, install a new package, or am awaiting a new kernel.
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You could just ssh into their machine or use No Machine. I use ssh for my Debian server and my wife’s laptop at work. Never had an issue, yet.
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That would work if they left it on, but they don’t. But it’s not that big of a deal, I just turn it on, run the update and am done with it while they are at school.
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This is especially true when you only use your machine every six months.
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The thing is, on my Arch installs, I think of nothing else, it seems 
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I just keep looking for them. 
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Mostly, I update once a week, as was mostly recommended for beginners. For the first time, today (8th of June) I am going to update an EOS system that was not updated for a month (since 4th of May, because internet connection was cut off).
I am going to use the command UpdateInTerminal, as suggested by Manuel above, and let’s see if all works well.
Updating after more than one month went fine and without any issues using the command UpdateInTerminal. 
My big fear when starting to use EOS was that updates would break something which I, as a beginner and n00b, would not be able to fix. After 16 months of using, I can tell that I am glad to use EOS.
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I just went a half a week without updating, and it was torture… We were switching ISPs and one service ended before the new equipment came in, so the only internet I had was my cellphone’s data for the past several days and I only have a 15gb tether allowance, so I didn’t want to spend it on downloading updates. But today all is better, I am now able to update at will.
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Yay!
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A glimpse to troubleshooting
Be prepared!
It is a good idea to be prepared for update problems because they do happen sometimes (but fortunately not too often). Below you can find a couple of tips for that.
Terminal access to a system
There are ways you can access your system even it doesn’t seem to boot normally or you cannot log in with the graphical interface.
For example:
-
Use a TTY (a terminal without GUI) by pressing e.g. Ctrl-Alt-F2 or Ctrl-Alt-F3. You’ll see a full screen terminal and can give practically any terminal commands. You can test the TTY already now. To get back to the GUI, press Ctrl-Alt-F7 or Ctrl-Alt-F1.
(These are typical key bindings.) -
Use arch-chroot with the EndeavourOS USB installer drive. More info here: https://discovery.endeavouros.com/?s=arch-chroot
The idea for both methods above is to be able to get a terminal interface and use terminal commands to explore and fix the system.
Exploring system to find problems
Here’s some commands that you could use for examining the system:
-
less /var/log/pacman.log
This shows e.g. what packages you have recently updated or uninstalled. -
inxi -Faz | eos-sendlog
This sends useful hardware info about your system into a network service.
Simply show the returned internet address here and other forum users can help you much more easily.
See also: https://discovery.endeavouros.com/forum-log-tool-options/how-to-include-systemlogs-in-your-post
What else can I do?
If you have problems solving the issue(s), come here and ask for help!
Practically always there are people here who have encountered and solved a similar issue before. They will help you and you’ll discover the friendly tone in the answers as well.
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I just restored my 4 weeks old EOS installation without any issues. It downloaded 3,9gigabytes of updates and system is still alive 
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