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We're not doing an overflight. We are flying from Eilat to Cairo.
Last time I was in telaviv there was cessna citation US registration flying to cairo. They told me they had no problems, but in the end they had issues getting a clearance, and getting flight plans filed.
I think was more due to the handling (or lack thereof trying to do it themselves) than the actual issue of going to cairo.
Do NOT let the Israelis stamp your passport. If you do and you go to a Arab country you may incounter some delays.
Also pays to take 2 passports, just in case.
That is a bad idea. I know a couple of people who have had issues because of that. Whatever you do though if you carry two passports (or more) and a Customs guy asks if you have multiple passports ensure you say yes.
I had a British co-worker (dual British/USA) taken away in cuffs at GRU a couple years ago when the Customs guy noticed his USA passport (he used his Brit passport as they don't need visas) popping out of his briefcase. He got sent out on the next flight back to the UK. Given he had lived in the US for 25yrs and maintained no UK residence he had to then hop a flight back to the US.
Also pays to take 2 passports, just in case.
That is a bad idea.