Just as a note, when I first read the section 5.2 of the FAQ I was also a bit confused. The line "Compiling your own system as a way of upgrading it is not supported." made think that maybe following the -stable branch wasn't supported. But after doing more research I figured that following -stable was good practice and it was the most recommended way of following the patches on releases.
English is not my native language, so I thought maybe was the reason why I found that particular section confusing. I think that becomes clearer in some part of the document, I recall reading something about changing versions being what's defined as upgrade. But making it clear to begin with is probably a good thing. So I think the section would look better if the line Compiling your own system as a way of upgrading it is not supported. was changed to something like: Compiling your own system as a way of upgrading (e.g., going from openbsd 3.9 to 4.0) it is not supported.