My knowledge of how transmission works is fairly limited, but I have been reading a lot and this is what I can add to the topic.
Transmissions with automatic syncros's let the syncro's to match engine speed and geer speed.
Say, you're shifting from 4th at 5K rpm to 5th and rpms drop down to 3K rpm. If you simply jam it in the geer, you do not give the syncro time to match the speed, therefore higher syncro wear and later on grinding. It might be an indicator of a syncro not doing the job 100% right; if this keeps happening you might end up damaging the syncro and then the 5th geer over enough time; 5th is the smallest in the tranny and is most vulnerable if you push it.
I've heard a lot of good things about Redline, too. If you use Redline and "baby" your transmission a bit, you might be able to forget about the problem forever.
If you would like more details, I can post the whole "spiel" on why's and what's. This information has helped me to understand quite a few things.