Say a feller was to forgoe re-upping his subscription this year. But did get back in the game next year. Would he have to pay twice as much for a subscription next year? And/or would that get him yet another year of updates...as well as all the updates he missed while laying out? How exactly does that work?

My understanding is if you wait n months you miss out on the updates for n months. All updates are cumulative so when you start your new subscription you're going to get everything you missed. I've been using Cakewalk since Cakewalk 1, but I haven't upgraded to each version. Over the years I've skipped a number of versions. In the past there was no penalty, and least when I skipped versions. I believe that is still the case. Currently there is a deal to upgrade so if you wait the price does go up. For $99 I'm going to upgrade since I use Sonar on a regular basis.

When you buy in again you will get the most up-to-date version including all the upgrades you missed. There may be some special Anderton content that you won't get, such as loops and samples etc. I have no idea if the price to renew your subscription will be the same as a person that is doing continuous renewals. I wouldn't think so because there has to be some incentive to stay current.
 
I'd drop a line to the suits Ol' Pal.