Hello,
So my friend and I are doing a year long trip around the world. We just kind of pick and choose where to go along the way. Either way we wanted to visit Syria. We travel from Egypt to Jordan and then on to Syria. We did not arrange a visa before we left the US on this trip. Basically you can hop a cab/shared bus to the border it was 10 JD (about 15$). When you arrive at the border you just fill out a form, give them a photo copy of your passport ans wait. We heard stories of people getting harassed at the border waiting for 6 to 8 hours and getting turned around. They asked us how long we wanted to stay and what we do for a living, etc. We waited 1 1/2 hours payed $16 (the amount changes by nationality) and where on our way with a 15 day visa. Not sure if the visa can be extended. It was actually very easy.
A side note is that our Hostel in Amman told us that they has sent about 13 Americans to the border in the same fashion without a visa and 12 of the 13 made it in. They also said that for other nationalities it is a non-issue.
Also it is Ramadan and kind of a slow time for travelers. Not sure if that has anything to do with it. So the moral of the story is go to Syria. Damascus is amazing.
Cheers,
Sebas

