I'm not a regular user (just toyed with it in some VMs) so I can't vouch for how the updates do, but I was impressed with the overall level of polish. It's an Ubuntu-derivative based on LTS releases so it lags a ways behind the cutting edge.
EDIT: looks like elementary OS 5.0 "Juno" is in beta and should be out soon. This release is based on Ubuntu 18.04 LTS.
Not recalling much repeated terminal intervention, though there were a few safety nets that I immediately turned off the moment I had it installed (I think related to package manager installations?)
Dropbox did not work well.
Desktop engineering is hard (as Microsoft are demonstrating). There are a very small number of really good desktop distributions (Fedora, Solus, Ubuntu Mate, may be a couple of others), which are not inconsistent or half-assed, but the side-effect of Free Software is that any motivated developer can have a go and put out their own distribution.
I'm fine with this in Linux, because it's built by people who donate their time for free, and might not be experts in UX, etc. But seeing the same in a commercial OS that Microsoft wants you to pay for is unacceptable.