Hi,
I’m currently using Core 1.x
Not really sure if I am currently missing anything from the current version, but I understand that the support of 1.x will not be there forever. So my question is this: how smooth is the transition - both for me and my visitors? If I only do a couple of posts per month, is the transition worth it at all?

It probably depends on whether you are using any extra addons, extensions, etc. as not all may be compatible with 2.0

We have sites on both 1.6.x and 2.x, and while we are very happy with the improvements in 2.x, I would say it’s not necessary to upgrade unless you have a specific need to, IMHO. If you’re only doing a couple of posts a month and you aren’t missing any functionality in 2.x, stick with 1.6.x and avoid any headaches.