I don't use FreeBSD anymore, but something that always bugged me when I did was the issue of having to switch package repos from "quarterly" to "latest" and back again to be able to install certain software. This isn't clearly spelled out for new users, there's no mechanism to choose which repo you want in the installer, and it's assumed that any FreeBSD user just already knows about it and how to deal with it. It's clunky and annoying at the very least, and I feel it should be brought up during installation.
While the Handbook documents *how* to switch from "quarterly" to "latest", it doesn't explain that some packages are not available in one or the other, something that can confuse new users expecting all of their normal FOSS apps to be present in the package repo.
This was brought to mind while reading the Sylvie review by @distrowatch this morning.