How much support do you plan on getting? The old releases don't really turn into pumpkins. Yes, every two or three major releases, they end up with a minor release that adds something to libc where binary packages from X.2 won't run on X.1 or X.0. But this isn't usually a huge deal for servers if you follow this plan:
Use FreeBSD as your stable base, but build your own binaries for your main service / language runtimes. If you build once and distribute binaries, keep your build machine / build root on the oldest minor revision you have in your fleet. When you install a new system, use an OS version that's in support and install any FreeBSD built binary packages then.
You do have to be prepared to review updates to confirm if they need you to take action (many to most won't if you are careful about what is enabled), backport fixes, build packages yourself, or upgrade in a hurry when necessary, but you don't often actually need to.
I don't think this strategy works for a desktop deployment; there's too many moving pieces. But it works well for a server. Most of my FreeBSD servers for work got installed and never needed an OS upgrade until they were replaced by better hardware. I did have an upgrade process, and I did use it sometimes: there were a couple kernel bugs that needed fixes, and sometimes new kernels would have much better performance so it was foolish to leave things as-is. And a couple bugs in the packages we installed; usually those didn't need an OS upgrade too, but sometimes it was easier to upgrade the handful of old servers rather than fight everything; choosing battles is important.
Or you can go like Netflix and just run as close to -CURRENT as you can.