Thats rather unfortunate. I think you can use Homebrew to pull in newer stuff, though, but I haven't tried (I don't host stuff on my MBP, I use my Linux workstation for that).
I'm sure you could, but bear in mind that several OS X Server services are built on top of the system Apache and its configuration file structure, so you probably don't want to replace it with a package manager-built version if you rely on any of these services.
On the other hand, it wouldn't be too hard to build and install a version of the SSL module compatible with the system Apache linked against a newer OpenSSL version, however, and I wouldn't expect this to break Apple's services, at least not until you install an update that either breaks binary module compatability or clobbers your tweaked module configuration.
I don't use Homebrew, so I couldn't tell you if it's capable of building modules for the system Apache, but building the SSL module "by hand" for system Apache with Homebrew OpenSSL should be straightforward enough.
