On further review: Thinky thoughts about 13.10, "Wayward Sisters." Mild spoilers ahead if you haven't seen the episode yet.
casey28 has
convinced me that it's not really all that weird that Sam and Dean didn't find themselves right next to the rift when they woke up in The Bad Place. Kaia and Jack were also thrown pretty far from the actual rift. Maybe this rift was extra powerful because it was so fresh, and/or because Jack was involved in its creation. Maybe if they'd walked through the first rift right after it appeared, it also would have thrown them a long way. So okay.
But I still think they should have been able to find it. They didn't need to be rescued by a couple of novice hunters. Except, of course, that the plot demanded it. :-|
And now the poll!
Poll As always, please don't put spoilers in the comments, including casting information. Thank you!