There's another detail I think a lot of people haven't noticed. Someone from Cakewalk mentioned it yesterday.
If paying monthly, you need a continuous 12 months to go into the "keep everything" status. However, at that point, you don't need to commit to another 12 months. If you did just another six months, everything you get in that six months, you also get to keep.
The only time you don't get to keep everything is if you lapse, and then re-start the membership later. That then requires another 12 months commitment for all the updates you get
from them to become keep-able.
This also means that, say you lapse for six months, and then pick it up again, you get the last six months worth of stuff as soon as you re-start your membership.
This is all really flexible, payments-wise. I think it's a pretty good system.