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Italy. I'm lost!!!

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I've been really impressed with the helpful comments placed here by enthusiastic travellers so hope you can assist me.
* Planning a five week trip travelling from New Zealand to Italy for my wife and I and two teenage boys
* Typically trying to cram as much of Europe into this 'bucket list' trip as we can
So, the questions:
1. Is it ridiculous to fly into London, train to Paris, then to Marseille and then rent a car to do the French Rivierra drive into Italy or just fly into Rome and do the Nice and Monte Carlo portion as a side trip?
2. I wish we were that far advanced that we knew where we would be on any given night. But we're not like that so can we just rock up to any hotel and try and get a room or would that be financially impractical?
3. Love the idea of trains but don't like the feeling of being stranded with luggage. And since we don't know where we'll be from one day to the next, what's the recommendation with motor homes - supplemented with regular stays in hotels/villas etc
4. Keen to visit both sides of the country as well as going inland to Cassino and L'Aquila. Would like to sneak into Munich for a particular festival and maybe Switzerland. Will that be pushing it for a five week tour?
5. Will try and encourage the family to learn some passable Italian and we'll carry a phrase book but, in people's experience, is slow English (backed up with hand gestures) enough to be understood - in urban as well as rural areas?

Thanks for any guidance.
Cheers

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