I used to do very frequent compiler updates for... a rather large codebase, it's not too bad. Even then it's only a part time job for one person, for a more rea

I used to do very frequent compiler updates for... a rather large codebase, it's not too bad. Even then it's only a part time job for one person, for a more reasonable code base (like firefox) and a more reasonable update schedule (official compiler releases) it's even easier. Basically you just snap off a dev branch from some stable build, do the update and identify all the failures then go through each one. Take a little bit of time to identify the problems and fix them as you go. If something looks like it's beyond your expertise level or requires the special expertise of the "code owners" to fix properly don't bother trying to wrap everything up in a nice tidy package all at once simply use pragmas or what-have-you to disable the warnings for the smallest section of code possible and file bugs (at a relevant level of priority) to fix up the issue properly later. Every once in a while you'll run into an annoying hairball kind of problem that requires a fair amount of work to fixup (like, say, warnings in generated code or something) but most of the time it's fairly trivial stuff.