Hi ChrisIrvine,
Welcome to The PainterFactory!
The decision to upgrade to the latest Painter version depends on each person's needs and wishes, not to mention budget.
Painter 9.5 is a good version and includes a great deal of what you'd find in Painter X, though not everything.
Also, Painter IX.5 seems to be pretty stable which is a good thing. It's more stable in my experience than Painter IX was, before the Painter IX 9.1 and Painter IX.5 Updates were installed.
Enjoy the forums, and please show us some of your Painter work. It's always fun to see what people are doing with the program.
Cheers!
Jinny