I religiously updated Sonar, mostly because of some software they included like Melodyne or Dim Pro. I have haven't been very happy with the Sonar side for a long time now. 8.5 was my most productive phase. (I work a lot with MIDI). Since 8.5 it has been a constant battle against their changes.... Obviously you have to upgrade with ths newer PC formats at some point.
I have pushed back greatly on buying plugins and software, mostly because I end up not using what I already have. Eventually you are forced to uprade some things when support stops. On the upside, I rarely buy anything that isn't heavily discounted. I've been burned too many times by software companies. That being said, Scuffham, Orangetree, and Vallhalla Reverb are run by decent people and I would never pay anything less than full price for their products.
I am almost embarrassed at times by the amount of tools I have at my disposal nowadays .
I think back to the beginning when my effects were 3 DOD stomp pedals for guitar. I recorded on a Tascam 4 Track through an SM58 mic...a Casio CZ101, a little Yamaha RX7 drum machine and a Yamah Sequencer....it took forever and sounded pretty sad at best.
Now I can slap an entire song together in one or two days that sounds like it was done in a pro studio.
I swear sometimes I just buy new software hoping it will inspire me to come up with new songs. I'm not sure if that's good or bad....