I’ve used Georando a fair bit, but the DVDs for various areas, before it became like an “itunes” of mapping where you buy online
to try and answer your questions…
1) yeah, it’s software and data that you can save on your PC’s harddrive (either by buying whole regions on DVD 50-ish Euros a time, as I have always done OR the new buy online method)
2) if you’re just buying one or two bits of map (as appears to be the case for you), you need to buy the Georando “Liberté” DVD to install the software and then go to the website to actually obtain the mapping data, where you get the first 200km2 for free.
3) yes, yes and yes, it does all the same sort of stuff as MemoryMap
As for the Swiss and Italian bits… hmmph, you won’t get this from any IGN/Georando mapping.
For the Swiss part of the Tour de Mont Blanc you need the Valais map which is number 4 of these:
http://www.swisstopo.admin.ch/internet/swisstopo/de/home/products/maps/swiss_map/25.html
As for the Italian stuff, good luck.