I was looking into this a while ago.
Israel does not stamp passports, but gives you a separate immigraiton card which is stamped.
The problem is that Egypt will always stamp your passport, so a stamp from Taba in Egypt is as good as an Israeli stamp.
Jordan will stamp a separate paper when you enter, but then you will have no entry stamp for Jordan, only an exit stamp (and a visa). I'm not sure if officials in Sudan will look this closely, but it would be a risk.
As a separate issue, currently it is not possible for motorcycles or 4x4s to cross Sinai, so this is your major issue. The situation may return to normal though in the near future.
EO
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EurasiaOverland a memoir of one quarter of a million kilometres by road through all of the Former USSR, Western and Southern Asia.
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