In reply to Jeff Chandler.

Jeff:

Is there any way you can document your experiences with automatic updates and complex sites and describe what breaks? Is it core, is it a plugin, is it a theme that breaks?

Any site that uses any custom code at all would break every time an update occurs. Having to patch and re-patch file on each update (one per month on average) is a huge waste of time. However, there are few options, Wordpress does not have stable supported versions, just a single bleeding edge version, and everyone has to play keep up.

A security fix should be a security fix, period. It should provide only the files that need to get fixed, and should be applied. There should be no change in functionality unless there is an exceptional circumstance where a function is itself the security issue.

One of the issues for me is a lack of "hooks", places where code can be easily added to the most basic of files. Security on wordpress sites (especially those using Cloudflare or other "edge" providers) is very difficult, made harder by the fact that there are no hard coded points where extra code can be added to monitor access to critical parts of the installation. No, htaccess won't work (edge providers, remember), so I have forced on every update to manually edit a half a dozen files on each install to assure better security and logging.

A security fix should be a security fix, period. It should provide only the files that need to get fixed, and should be applied. There should be no change in functionality unless there is an exceptional circumstance where a function is itself the security issue.

Functional upgrades should be "full version" things. The .1s and .2s should be fixes to those functions (without adding new). The reminder bug for those versions should be able to be disabled or ignored. If they are patching something because it's a security issue, then issue a security patch.

Right now, having to make a full site update twice a month per site is a full time job. (twice because the themes and plugins are always late). Even an hour per month per site, over a couple of hundred sites it more than a full time job alone. Either I contract that out or hire someone at cost, or I do it myself and lose the time that would be spent doing something profitable (or enjoyable). Too many updates, too many versions... it's hard.

A personal suggestion for wordpress: STOP. Build out a stable version (say 4.5) and stop adding features and such. Then go away, and work on wordpress 5. Clean sheet it if you want, whatever. Don't come back for 6 months until you have a fully functional product. When you do release it, allow for and support theme and plugins versions for 4.5 (ie, allow there to be a stable 4.5 version of everything in the WP universe) and support 5.0 and beyond as itself. That will let you clear up the code, make major overhauls in how things work without worrying so much about legacy coding, and at the same time provide a stable (and supported) version 4.5 that would be perfect for users who don't want or need the bleeding edgem but who do want to have a secure and supported version.

It's time to move forward.