It depends on the package really. Sometimes you're better off without the fixes that occurred in the last 2 years if it means avoiding the new bugs in the last 2 years.
IMO the more you try to stick to the latest releases, the more important it is to continue to stay updated. but every upgrade is a chance for new bugs or just breaking changes, so for new users starting with a stable distro is a good choice.
.. except for browsers, where you both need the newest features but REALLY need the newest fixes.