CityTrader
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It is only $79 in the US. Upgrading to Yosemite shouldn't cause a problem with Parallels.
It's upgrading Parallels, Then upgrading windows ( they charge I guess?) and then upgrading mac OS X - I wouldn't even know where to start, if my macbook could handle it all.
TBH it;s not worth it for me- I leave my macbook in my apartment in Mallorca and only use it for the 6-8 weeks i'm there. At home I use an iMac and a dedicated windows PC only for proquote