I owned a gr33 and currently own a gr55.
I preffered the gr55 better. I think it has better sounds and more of them, but the difference isn't that significant. It seemed to track better as well. The 55 does a slew of things the 33 does not. The COSM guitar modeling is a whole different world of tonal possibilities that the 33 doesn't offer. You also have alternative tunings, FX processing, and amp modeling.
The 55 is a very durable all in one unit that is fantastic for playing a small gig and giving you a ton of options.
That said, if you want to upgrade for the purpose of recording midi into your recording software, get a Tripleplay. Its faster and cleaner than anything Roland has put out, see it here .Its definitely a worthwhile upgrade for the price if you value fewer missed notes and better low note responsiveness. Its also can be used on different guitars quite easily.