Sure I'd pay for an update - heck I've done it before.
I've still got my Roland VS-840 which I was able to turn into a VS-840EX by using a software update on ZIP disc Roland produced - I think it was about $55.
I still use it for effecting and routing my analog guitar rig (Boogie StuPre + Lexicon + TC gear) using its digital out into my computers' digital in.
That being said - I'd be EXTREMELY leary of updating a $1400 piece of equipment using an illegal download from a torrent site - brrrrr, no thanks! Legit all the way.
You need to have recourse from a manufacturer when it's a piece of gear you rely on and use to run your music business.
Face it - things are tough all over. That earthquake in Japan just being one problem. My previous day gig was IT in the securities industry. Around 2005 I moved to IT work in the real estate sector just before it blew a gasket and things got very bad - I don't really know if things will ever go back to the way they were but I do admit the VG-99 is an expensive device - it can do some spectacular things and it can do some things that other devices have probably eclipsed it some. But most of the guitarists I know are not using this type of setup - they've got a Strat or a Les Paul and a Fender or Marshall amp and some pedal effects. Or a more modern guitar and some type of low to medium priced modeler.
But I'm not "most guitarists" (link to footage from most recent gig):
-Yes the market is in a down economy.
-Yes these are specialty devices that are expensive (the GR-55 less so but still a fair chunk of change).
-Yes, guitarists are arch traditionalists who don't often explore the far out reaches of sound but mine well worn "safe" paths.
-Yes, many guitarists are often seeking out the guitars and gear their musical heroes played. Only a handful of "names" seem to play the VG-99.
-Yes the guitarists who would buy a VG-99 would have their hands full exploring the box just as-is.But
in some ways Roland has itself to blame for the poor sales:
-Little to no marketing in music magazines for the VG-99. What marketing there was didn't play to the devices' strengths.
-The two ads I did see poorly illustrated the product capabilities and I didn't actually even think of buying one until the Premiere Guitar article plus Bill Ruppert's samples.
-The display kiosks I've seen for the VG-99 were only briefly operational. Just long enough to make me go "yeah, I want one".
-One was pulled out of the store I was trying it out in two summers ago and was never returned to the sales floor.
-That same kiosk started to exhibit display screen problems (not the VG-99 but the little video display that shows the capabilities with little buttons that played segments
of the video) so maybe that's why but...
-The other had a partially-functional GK cable and I would often find the kiosk and VG shut off or a salesperson pushed a half-stack in front of it so you didn't even know
it was there. You had to look for it.
I always had before made sure these things were on and working and I'd sometimes demo the stuff while in the store but it's sort of a futile errand.
As far as the GR-55 - that device does appear to have a lot more interest and notoriety than the VG-99. The marketing appears more spot-on and just finding one to buy is difficult since the demand is still there. I don't rule out getting one at some point but I'd actually consider getting a second VG-99: I want to run four paths of COSM audio
at some point with my custom patches.
But maybe the market finds it a tough sell to push a product with a several year learning curve? Most players don't have the patience.
I've pretty much given up on the software update of old but if I can illustrate the nylon guitar hysteresis problem maybe they'll fix that one.