So, if you know ports and gentoo, is there significant common ground that they're kinda like each other, or are there significant differences - either in tasks performed or in outcomes that they are worlds apart? And, what drives you to choose ports and is it all compile and wait, 7 days a week, or what? Maybe I'm over simplifying things, what are the actual advantages/disadvantages? More than just speed/customizability vs compile cycling all the time?
Gentoo is a rolling release distribution, meaning there is no standardized release cycle. It was[*] also based on the need that you've got to compile all the stuff you want to use by yourself.
[*] Gentoo always shipped since a long time binaries for applications many want to probably use, but which do require quite capable hardware and lots of time to compile, like Chromium, Firefox, Rust, Libreoffice etc. Since 29/12/2023 though Gentoo is also offering daily binaries on X64 and ARM64 for all ebuilds in the official sync tree, which makes it behave here now in the direction of Arch Linux.
Gentoo is also opinionated in the Linux world due to not having systemd as default init system, instead it uses OpenRC.
FreeBSD on the other hand is a stable release cycle binary distribution OS, where you can compile stuff on your own, but don't have to. Sometimes though it might be a necessity if certain flags you want to use are not compiled in the default binaries.
So for Gentoo, until recently due to its introduction of official binaries for all stuff in portage, compiling most stuff on your own is the default experience. For FreeBSD it is entirely optional.
So far I had not much reason to use ports in FreeBSD, since its binaries with default settings work good enough for me. Portage though is another thing. Since it has to deal with tons of more complexity than ports has to do, it is much more prone to break.
The official Gentoo forums are full of questions of people who are asking for help, when upgrading something like e.g. due to OpenSSL, Python version or similar switch is not working as expected. And since Portage is written in Python, when Python is not working on your system any longer on Gentoo you're basically screwed. Also sometimes QA on ebuilds is not where it should be, and therefore they do not compile properly.
Anyway, managing a whole system with Portage is a fucking nightmare. Sooner or later in its lifetime it will bite you, hard, due to stuff not compiling, circular dependencies, gone ebuilds as dependency and other nifty things, even if not following ~amd64 and only amd64. Also be very sure to read "eselect news" regularly, otherwise you will be fucked as well.
Ports is not, because the default use case is to supplement a binary base system, not to run it. People who like to run all of FreeBSD using ports though on their own sometimes seem to run into similar problems like with Portage. Even then still though the release cycle of FreeBSD seems to make this happen much less frequently.