Hi zzzlumber,
Updates to WP are a good thing – many times they fix security holes, small bugs, or make little improvements to the UI. I’d be more worried about using a framework that isn’t kept up-to-date.
I’ve used (and built with) many Content Management Systems, and in my mind, no other CMS comes close. WP is incredibly flexible to build with, and there’s a huge community of people in the support forums and building themes/plugins.
Not all upgrades require fixing. The latest WP upgrade to 3.5 made significant changes to the handling of the media gallery, and this plugin makes significant use of that media gallery, hence the comments and upgrade. In my experience, most plugins I use regularly worked with 3.5 without any problems.
Stick with it – you can always wait to upgrade in the future – you don’t have to upgrade your site straightaway – wait until you’re sure all of the plugins you use are compatible.