Have they been coming out at roughly the same time every month?  If so....any ideas when the October one will be out?  Debating whether to go ahead and upgrade now, or wait until the next update if it's coming out in a few days or something....

I don't think anyone other than CW staff know when each version will be released and they may not know to the day until the day of the actual release. I would think if one were timing their purchase, the release date of the 12th release out would be more useful.

Well, there goes my whole logic base, then ;-)

The current Ipswich release is pretty sweet, so coming from X3 it would be a nice upgrade now. Honestly, with the current update/release model you'll always be a short time from the next update so trying to time things is futile.  
 
Cool, huh?   
 

Well..one good thing....I just found that the upgrade to Platinum is on sale at Audiodeluxe.com for $124.99
 
So, I think that cinches it....

Purchased :)

Updates have typically been right at the end of the month, but last month's was a good couple of weeks early. There have also been two updates some months (though only one major one per month).

Congrats!   While X3 was the best release in a long time, Platinum simply raises the bar (IMHO).
 
Just get used to the idea of there being a new update every month or so.  Some do not like this and feel that it's too much too often, while others (myself included) simply love the idea of something new each month.   If you happen to be in that second group you're going to love the membership program.   

Also note that you can defer updates if you like, and roll back if an update causes problems, it's all very flexible.

I almost didn't upgrade from X3e.  I'm sure glad I did.