By already configured: we mean that it
inherits your Alf's configuration.
No DRM is one of those that MR does not host, (We can only mention it, no further help allowed) so the Calibre Notice and update tool does not work. That does not stop you from installing it the same way all other Calibre PI get done. Preference Plugins.
Always read the release notes on the download page if you are using an old OS
Kovid always discusses Major coming changes that might affect existing plugins.
IF there are any USER issues with Calibre or its plugins, they will be mentioned here, usually within hours of release. So just check here
You do have me a bit puzzled.

Why are you waiting to convert
your books? (or were you including new purchases in this use)
Once converted, they are a part of your Library and just need to be delivered (USB or email) at a later date? That part (or if necessary, an OS 'file Copy') will always work. AFAIK Calibre has never removed a format support. Calibre 2.0 was limited to newer OS when it was discovered that it was unreliable under XP. There simply are no NEW 32 bit releases being made. All older 32 bit releases are still available for download
Staying as current as you can, means new devices and file types are supported.