I would like to hear some opinions and I'm not sure how I would grade the answers. If experts think this kind of question is not appropriate, let me know.
I maintain several Wordpress sites and yesterday I upgraded a site to 3.8.1 and as a result a crucial plugin stopped working. I tried to solve the problem myself and with the plugin support page, but didn't succeed. Anyways, this got me wondering if this isn't a major disadvantage to using Wordpress? Although most of the sites I've built are over version 3, I've been very lazy about updating them and now I'm a little afraid to do so. It seems like it will involve an enormous amount of time.
Because several of the sites I manage are located on a windows server, updating is more than just hitting a button and becomes somewhat time-consuming. In addition reading the update information for wordpress and the various plugin versions in order to decide whether it's necessary also becomes very time-consuming.
Do other open source cms's also suggest these kinds of frequent updates?
Is there another perspective on this that I'm unaware of?
I'd appreciate any feedback about this.