In reply to Phillip Hawley.

Phillip I think the disconnect can be put a little differently. You have drawn a conclusion that updates to WordPress core are not done with enough care toward backward compatibility.

I think the problem is expectation management. It is a nuisance when a site is updated and one or more things don't work. Everybody can agree on that. But this is highly dependent on the plugins you use and how your theme is coded. And even when update issues occur they are almost always overcome. This doesn't take away the fact that 3rd party code sometimes runs behind and that sites need to be maintained and maintenance sometimes requires work and diligence. All of that can been seen as a burden, especially if your expectations are different.

But, let's say you are correct in pinpointing the cause of your frustration. To make that observation - that WordPress itself evolves in ways that are lacking toward backward compatibility - you would have to be actually familiar with the code yourself and all the work and care that core developers put into it, just to make that particular diagnosis. It might sound offputting, but you'd need to be pretty familiar with the innerworkings of core development to really make such an acute diagnosis. I don't think that's the case here. I think it would be more helpful to focus on articulating the frustration you have so people can give better feedback on it, instead of complimenting it with a self-made diagnosis.

It needs to be said that it is completely unrealistic for WP Core to evolve - something all developers clamour for - and also guarantee that 3rd party code (which varies in quality) is going to work in every single case.

You can avoid all manner of update issues if you run a heavily customized site by adopting a better update policy: test updates on a staging server, have a system to rollback updates, let another party manage the particulars, pick plugins that are well maintained, support the plugins you use or rein in the amount of custom code running in your projects which reduces the maintenance upkeep costs.