Once upon a time I used to build the entire BSD package repos from source code every 2 weeks. It aint for the faint-hearted as lots of things could and would go wrong with using the latest and greatest for 3 code streams (latest major release, latest major -1, and latest major -2).
The issue with updates for old releases is less to do with building it, and more to do with testing it. Often with these older releases there is nobody around to fix any problems with them.
I still run WinXP on a 32bit PC that is not connected to anything as it's set up beautifully and has served me well for a while. It doesn't need anything more done to it for the role it performs.
If you want network connectivity then unfortunately you have to dance along to the tune that goes with having it.