I've got a serious oil leak on the passenger side of my 99 F150 5.4, enough that it is smoking from around the hood. The tech tells me it's the head gaskets leaking and it will cost $2000 to replace them . Does that make sense to any of you?

 

Makes alot of sense. Do a search and read about it till you drop. It's a known problem on 99 5.4 & 4.6 It is actually not a head gasket problem but a problem with the way the head was machined. To be more specific it was the way the head was removed from the surfacing machine. Replacing the head gasket is not a guarenteed fix and many have reported the leak soon after the repair. A more positiive repair is to replace the head or heads.