Hmmm, well if he gives you a key every year, why do you even want to crack it?
If it is for a friend or family or anything, why not using the same key?
Or are you just asking us to crack some random program and added a little nice fake story?
If it is because once you register it registers your HWID on their DB, then you/the other guy have to spoof HWID before running it.
If anyone does that, they probably can decently pack it and Olly probably won't be able to Debugg it, being therefore useless.
If Olly can debug it then from there all you have to do is read the ASM code, and either change the register values or modify the jumps. Of course it can get a little bit more complicated since it involves an external .dll which might contain code relative to the activation key, making it harder to crack, after all a .DLL it's not a .EXE and RE on DLL's it's a different story.
If the .dll it's just to install or to runt he program with a complementing library for the program to run, then should be just Debug and ASM reading.
Of course, I've seen lots of RATS and bots saying missing .dll...
Since your story is kinda weird, I'm not sure I'll download it and risk myself to contribute as another zombie.
I think I covered everything I wanted to say.