No real sticky points - just a few challenges
I Did the route starting Cape Town Nov 15 and ending UK june 16. I did it by myself and I can assure you that you don't need a group - other than the risks of traffic I never felt threatened.
So heres my take on your points:
Sticky 1 - Egypt - Turkey or Egypt - Greece is relatively easy despite what you hear. There is regular Ro-Ro shipping from Alexandria and you can get a ship with a weeks notice. You will lose your bike for 2 weeks whilst it clears and travels and you have to fly. Total cost for shipping my bike was US$900 including all the shipping agent services. For more info search the shipping database on this site where I posted all details - and I put a post on this site with some info as well.
Sticky 2: Consider getting a Sudanese Transit visa instead of a tourist visa - much easier and I found adequate time to cross the country and see the sights. These are valid for 2 weeks and available within 24 hours at the Embassy in Addis Abbaba (where I suggest you also get your Egyptian visa - 3 days). Again I think I posted on this - If you cant find any more detail send me a PM and I'll send you more details.
Sticky 3; Supposedly were security problems when I was in Ethiopia - but I never had any issues (except with street kids in Addis who are more a nuisance than a real threat). Locals in the country are exceptionally friendly and helpful to travellers - especially in the tourist areas where they are keen to politely part you from your money.
Sticky 4: You now have no option but to use the road crossing, the old ferry service up the lake is still running but only for passengers etc - The road crossing still involves a very short river crossing by ferry. The border procedures take ALL day (8 hours) but its the same for everyone and aren't that difficult and there is no need for fixers. Also be aware it is not open Friday (How do I know?)
Stick 5 - Nil Issues
Sticky 6 - I shipped my bike from UK to Cape town at the start of the trip. I used MotoFrieght in London and it cost 700-800 pounds. Again full details are in the shipping database.
Bottom line - I found the trip much more straight forward than I imagined - and it was easy to collect all the info I needed for the next country or border crossing on the road from other travellers. Border crossings are not "a nightmare" despite what might read. With the exception of the Sudan/Egypt one which was slow (but still good humoured) I got through all the other in an hour or so with minimal problems (common problem being finding someone who had gone to lunch)
My blog has more detailed info if you want to trawl through it or PM me if you have something specific you want to ask
Enjoy
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