Drupal is a moving target.
That is kinda cool. The new stuff always blows me away.
The problem is never with upgrading core, it is in the modules. I just have to hope the modules I need will eventually be available. I always start out lean and mean, but the cool stuff seems to creep in. Still, that's fine if it is just me. If a feature goes away in the future, I will understand and forgive me.
It is different when I am setting it up for someone else. I do want to hand them something sexy, but at the very least I want it to be simple to use.