Glad to put you on the right track, Jamie, and congratulations for persisting with it.
Update policies... what a minefield. I have worked with several different update policies, and they have all been challenging in their own way.
One updated with every minor version release, staying current, but this not only created issues with maintaining the Moodle, it also presented time issues, with pressure being placed on the staff who were responsible for doing the work. Every month, basically, one of them would be up at 1:00am on a Sunday morning, to upgrade the Moodle. Dramatic failure when one guy said he wasn't doing it any more so sack him or find another policy! They then changed to twice a year and few complaints since.
My small Moodle upgrades once per year, during the annual holiday cycle, and they are happy with it. Works well for them, but is a small Moodle.
Another I worked on will not update top the latest, but to the previous latest, twice a year. That is what they choose, and no-one has ever explained the reasons why. A guess would be that the latest may hold a bug or two, possible, whereas the previous latest has been tested, well used, and would have had any major surprises removed.
All others have been variations on this. My schools Moodles are all controlled by one Moodle Partner, sensible, but getting things done can be an issue. Just to get the progress bar available has had to go through so many layers of bureaucracy it is ridiculous. They update once per year, i understand. Never bothered to confirm this.. but... as they say, not my problem.
This is just for your information, and anyone else who reads this. My bet would be there are so many different attitudes and policies out there that, essentially, it has to be an enterprise decision. That is, what is my enterprise? what do I want it to achieve? what are the best tools available to achieve my enterprise goals and so on. If you have a huge Moodle, like OU, for instance, you will need a consistent and definitive policy, but if it is 'Greta Garbo Home for Wayward Boys and Girls', then it would likely be, "when I think of it." Needs must, I suppose, but I suggest any longer than a year behind, you are probably putting yourself under more pressure than necessary.