As long as your current software isn't "limited", and works properly, than I honestly feel it isn't an emergency to go out and buy the latest software? There IS alot to be said about the latest software. It is more than likely more refined than what it replaced. Easier to use, more options, you name it. With all this comes the pricetag, and not everyone can afford it unfortunately. When I started out, I purchased a V.E. cutter, and a copy of V.E. Master software. I've since upgraded the cutter, but believe it or not still use the same software (and same version) that I did when I started!
With the software being as old as it is, I've got keyspans, software dongles, and all kinds of other things I had to do to get the software to work with my more modern Mac G4, BUT, the software STILL does everything that I need it to do. I've got a Versacamm and a newer copy of Flexi, yet where I've been with that software for so long now, I just keep goin' with the flow I guess?
"If it isn't holding you back, I would stay with what you've got for now at least"
Good luck! -Dave