Without reading anything but the OP,
Caravans - the problem with these was that they were really easy and gave out tonnes of stuff. I have no problem at all with there being decent encounters to loot but there must be a corresponding challenge to it ... else its just handing out high tech gear.
When the new encounters come in there will be Mutants, NCR Army, BoS and Enclave patrols where decent loot can be put, what needs to happen is these all need to be played with until they are hard enough to beat to deserve this stuff.
For caves, I'm sure Lexx has said on the forum that he's doing stuff for this at the moment.