Garmin is notoriously bad with their software updates. Many people complain about issues lasting years and no resolutions, no comments from garmin and when releases are made they are inconsistent.

My experience has been that I've been hit by a few bugs like the auto adjusting issue (would get the tire size wrong) on the 305, ending courses early (305), crashing on courses (705) and a few other random ones. At this point my 705 seems to be fairly stable but the calorie count is still darn near useless, which was commented on from the start of the 305 and the impression given by garmin was that the 705 would resolve (which it did now). The 800 (and the 500) finally improved on calorie usage calculations but many people report it to have potential errors, clearing the devices seems to work.

Courses and virtual partner stories are all over the place from people who have no issues (VP always worked for me and I ride with groups vs courses).

200 bucks to upgrade.. It costs about 350 from some places head unit only. If you want the graphical interface and the mapping, sure, go for it. Use open cycle maps to get a free map set though, no reason to pay for that stuff. I've gotten myself lost before and found the maps to be useful