But if all applications use the same OpenSSL that is managed by dpkg+apt (or something similar), a single update will fix all applications.
Personally, I don't think that this problem can be solved without losing the advantages of bundling (robustness, reproducability, binary portability to other distributions).
e.g. Windows supplies KERNEL/USER/GDI as builtins, but doesn't supply libpng.
Pretty much the whole point of an OS is to provide a guaranteed stable base. Anything that isn't guaranteed or stable should be bundled with the app.
http://www.cvedetails.com/vulnerability-list/vendor_id-7294/...
The thing is that Linux distributions traditionally don't make any difference between the OS and apps. Everything is split into relatively small packages. Like everything this model has some advantages (e.g. security updates) but also some disadvantages (it's harder to distribute/install software outside the distribution).
It's how you ship 1000 different versions of the same library and have no idea what to do when they need to be upgraded. It's just a terrible way to manage a system. Easier doesn't mean better.
Be aware of typical Linus swearing: https://www.youtube.com/watch?v=5PmHRSeA2c8#t=358