You may need to install older versions if they contain plugins etc that you want to continue using, you may also be able to achieve that for some by doing a custom install and selecting only those items
I believe it is advised to install the previous versions first for various reasons, like a newer version of something being overwritten by an older one perhaps.
With the command center - all updates are accumulative, so there is no need to install them consecutively I believe, there may be some things that were released for a certain month, bonus/special stuff which will/may be required to install separately.