I have used the updating route each release since I started using Slackware with 10.0 or 10.1.
There is no simple one point-click-and-install. As you mentioned, reading the change log and related docs is required to be successful. Typically there is at least one "gotcha" in the docs.
Usually something like adding a new group or splitting a package.
I don't recall any significant mishaps although I have overlooked or misunderstood some of the "gotchas" that have appeared with each release.
I use a partition scheme that allows me to avoid worrying about user data files, boot files, etc. I use separate /boot, /home, /home/public, /tmp, /usr/local, and /var partitions. I install the root tree and /usr on the same partition and that is the only one that gets updated.
Installing fresh is an option too.
I find that both options require about the same amount of time for me because with my partitioning scheme, really all I need migrate are my configuration files and system scripts.
If you are not picky about config files and scripts and such then a person can be updated in an hour or so. If you have accumulated a collection of customized config files and system scripts through the years, then I would say either route is painless but is a wee bite tedious.
I use virtual machines and some testing partitions to hone the process either way and that reduces the potential for serious errors.
Either way, if you are comfortable with computers and the Slackware design, then keeping one family box stable with the recent release will mean a few hours every 9 to 10 months or so to update to the next version or install fresh.