Hello!
I am using a very old version of Moodle and want to update it to the most current. My only fear is risking losing any items or if this big of a jump will effect the content. Does anyone have insight?
The way to reduce the risks and problems is to make a copy of the site and perform a test upgrade first. This allows you to identify and resolve any issues during the upgrade, and you can test the upgraded site to identify any problems the site's users (admins, teachers and students) might face.
Functionality that's part of "core" Moodle I would expect to work. Functionality that's provided by any plugins on the site is down to how well that plugin supports the target Moodle version. Identifying such issues is one of the reasons for a test upgrade.
You may have a motivation for choosing Moodle 4.1 (for example: a specific new feature) but you may wish to consider instead upgrading to Moodle 3.11 for the following reasons:
- it's less of a big jump in versions;
- it can be upgraded to directly from Moodle 3.7 whereas Moodle 4.1 requires Moodle 3.9 or later;
- it has security support until November 2023, and
- it supports PHP 8.0.
+1 to Leon's response ...
2 cents more *IF* the clone is on Linux OS with git installed ... git updates/upgrades to core code will make the 'moodle march' much more accurate because code stays in place ... none of the rename, download only to have to turn around and upload, unzip, copy back, etc. (too many moving parts which is prone to human error).
https://docs.moodle.org/401/en/Git_for_Administrators
'SoS', Ken