Thanks for your insights markharf, Tim_A and eurasiaoverland. Sorry I haven't been able to reply earlier. Been busy with work.
As I said earlier, it is a rather ambitious plan to say the least, but I am open to suggestions, information, alternatives, which you guys have so generously provided. Some have even said that I shouldn't even bother to attempt such a trip. Positive criticism I can appreciate and welcome. Plain old criticism however...
TimA I would love to speak to your friends about their trip. Could you please PM me their contact details. I have yet to speak to one of the guys I found through this forum (Saleh, I don't know if you know him).
I have changed my initial route seeing as the Moroccan - Algerian border is permanently closed. I am looking at two different routes now.
1. Getting into Italy through Tunisia
2. Or Europe Via Iran
I don't think there are any restrictions on bikes entering Saudi. Even multiple entry tourist visas are now possible, given the new government and the 'forward' approach to make Saudi Arabia a more tourist attractive destination.
Syria is still the problem bit, mostly on the 'return' leg of the trip.
Looking into the Libya part of the journey. I have a friend there so have to check with him as to how things are on the ground, rather than just relying on what the media is saying.
Still researching other things. Shoot me a message if there's anything you would like to add. And thanks again for your positive feedback.