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Advice on Jordan/Masada Itinerary

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My sister and I are planning a trip to Jordan and Masada in March 2015. Our tentative itinerary is below.

Does this itinerary seem doable considering we want to see Petra at night on the first night (3/11) and that only happens Monday, Wednesday, and Thursday?
What is the best way (taxi, driver, bus) to get to Masada on 3/14 crossing at Eilat? Do we need to cross back at Eilat or can we cross up north closer to the Dead Sea on 3/15 since that is our next destination?
What is the best way to hire a driver?
Anyone have accommodation suggestions in Amman, Dead Sea, near Masada, and near Petra? We prefer 4-5 star.
Thanks so much.

Itinerary:
March 7 (Saturday) fly to Amman
March 8 (Sunday) arrive Amman, stay Amman (hotel? Crowne Plaza?)
March 9 (Monday) visit Amman, stay Amman
March 10 (Tuesday) day trip to Jerash, Madaba? (Stay Amman)
March 11 (Wednesday) travel to Petra stopping at Crusader castles, night Petra, stay Movenpick or Kempinski (?)
March 12 (Thursday) day in Petra, travel to Wadi Rum, stay at Bait Ali camp (? baitalicamp.com)
March 13 (Friday) visit Wadi Rum, travel to Masada (where/how to cross and stay?)
March 14 (Saturday) visit Masada in morning, travel back to Dead Sea on Jordan side (hotel? Movenpick?)
March 15 (Sunday) Dead Sea visit, travel back to Amman (hotel? Or straight to airport for 3am flight 3/16)
March 16 (Monday) travel back to US

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