I've never crossed land borders in the Middle East [with the sole expection of UAE-Oman, which is VERY easy, VOA system

], but my understanding is that there shouldn't be too many issues going between the Muslim countries. It's Israel that's the problem. Jordan itself doesn't have much of a problem with persons that have visited Israel to cross the border but Syria is very strict about it, and Lebanon may be too. Also, right now the Lebanon-Israel border isn't the safest place in the world- is it closed at current? My memory fails me..
Anyway, if you really want to travel overland then go through Syria. However, this depends on how much time you have and if you even want to see anything in Syria. If not then yes, your best bet is probably to fly.
As for visas, you may want to check with your embassy for that but I was under the impression that most Middle Eastern countries do Visa-On-Arrival. This may be completely wrong however

Always best to check!
Sarah: Little girl, big dreams. Currently living in Scotland
British born, Barbados raised, slowly but surely getting out there. One day..
Next trips: Australia Late March-April; Europe Late June-Mid August