If your needs aren't time-sensitive, a lot of people wait until a special comes along and then pounce on it.
Propellerheads is a company very much like Cakewalk, with cool people. I'm sure if you run into any issues trying to transfer a license, their support will help you out. Companies tend to appreciate people who buy software rather than steal it, and respect the value of a company's work.
And...sorry about your loss. When there's a loss in my life, I try to be grateful for the time I had with that person rather than regret the time I won't have. 34 years of a marriage rocks...congrats to both of you.