Wait, wait!
4.1 was an LTS
now an Unsupported Moodle Version
Highest is a 4.1.19
4.1 is an LTS.
Security supported untill Dec 2025
See https://moodledev.io/general/releases (screenshot as of now, 14 June 2025 embedded below):
True, the highest release so far is 4.1.19 https://moodledev.io/general/releases/4.1/4.1.19, released 9 June 2025. But more (4.1.20,..) will be released till December.
To the OP, you wrote:
I’m starting to wonder if I’ll need to skip this LTS version altogether.
Moodle upgrade path allows you to skip many versions. See http://www.syndrega.ch/blog/#php-and-dbms-compatibility-of-major-moodle-releases for an overview (the column "Earliest from").
Would it be safer to stay on 4.1 for now, or consider moving to 4.4?
Safer in what sense, more secure? Or, lesser chance of you breaking the upgrade? The 4.x series is well tested. So, AFAIC if you break the 4.1 LTS to 4.5 LTS upgrade, then you might break 4.1 LTS to 4.4 as well.
P.S. This is a diversion from the original discussion, Moodle 4.5 LTS breaking *older* versions of Moodle! I gave this one a new title. I suggest you add the information related to those "issues" as explained in Read this.. before you post and the helpers will follow up from there. In the mean time the moderators might decide to split this discussion.