Approximately once a month. I've been trying to find out the status on the first one, but apparently Boston has been shut down AGAIN from even more snow...I experienced the edge of the storm yesterday driving from New Jersey to Tennessee, the Blue Ridge mountain roads were nasty. Took me 17 hours...should have been 13 max.
I believe that pretty much all the features/fixes/content for the 1st update are done, but if the QA people aren't in the office, that's a problem. I guess the good news is that if there is a problem, it will only be a delay.
I prefer a more permanent solution, like moving Cakewalk to Maui...then hopefully they'd need me to come over and consult during the winter.