I hope the following is of some use even though I can't answer your first 2 questions. Unless you have an institutional license for W7 you might as well go directly to Windows 8 without passing GO and collecting $200.00.
Why are you considering a MAC? PCs are cheaper and way more programs are written for them than for MACs. Also PCs can run Linux if you get burned out on Windows, in fact you can set a PC up to boot up with different OSs (but I think MACs can also run Linux). AND you can actually work on a PC ie install additional drives, monitors, swap out transformers, add fans etc etc. even if you are not a "techno-geek" but just have some common sense (having one or more PC-savvy pals don't hurt either)
I'm thinking of buying a mac but I haven't decided yet.
How does programs like chessbase and deep fritz perform when installed with for example VMware?
Should I go for Parallels or VMware?
Which version of windows is best to use? I have institutional licence for most versions.