I deleted my 150 hour save, wanted to start fresh! (As the bugs on the old save/patch ruined my playing experience, my save was over 15mb, and constantly crashed)
Anyway........!
Downloaded the new patch, started a new game on hardcoe mode, got to Novac, wanted to earn a couple of thousand caps from Cliff Briscoe, id played 5 games, maxing the amount we could play for, and winning every game, i quit so i could buy more stuff from him, now the option to play caravan isn't even there anymore ?
He DOES have money, ive brought stuff from him, he has 500+ caps, ive waited 3 days, etc
Still nothing..
I never had this problem before v1.02 was released..
Could anyone help me out or give me a possible solution ? Thanks!

Try deleting the patch.