The only advice I can give:
- IF you decide to upgrade to CC3 you'll gets lots of symbols. Check them out first and then decide if you want any of the Symbol Sets.
- City Designer 3 is very great addon I think, but only if you plan to map a lot of cities, towns or large neighbourhoods.
I have no experience with CC2, the Tome or Fractal Mapper. When comparing maps between CC2 and CC3 the maps made with CC3 always look better. I am not sure if the features are a lot better or just the graphics.