It has nothing to do with the caravan being robbed (don't worry there are a thousand contingencies and options to fix/work around that loss). In fact, it doesn't really deal with any ingame events.
The unfortunate occurrence centers around the fact that the following phrase was said (paraphrased):
"God damn it, the crafting skill was removed in 4e, how the hell am I supposed to fix this broken wagon?!"
I'm almost positive that I gave everyone the following pieces of information:
- You have spare wheels in the caravan
- They won't immediately fit on the woman's wagon and it will take some time/work to make them fit
- They won't fit because the holes in the "hubs" of your wheels (spot where the wheel connects to the axle of the wagon) are larger than the woman's.
In other words: In my opinion, skill checks are almost never needed. So please avoid going to them immediately. Don't worry, I'll tell you if you need to pick up the dice. ^_^
To belabor this point a bit further let's talk about "lockboxes".
WoW and other video games, being programmed, rely on specific instructions to accomplish specific tasks. The easiest way to do this tends to be "if your character has THIS skill it can successfully perform THAT task," but D&D isn't (and shouldn't) be like that.
If you find a lockbox in D&D you can do all kinds of thing with it! You can try and pick the lock. You can try and find the key. You can get a pry bar and try and pry the lid off. You can drop it. You can run it over with a wagon. You can set it on fire. You can crush it underneath the ass of a stone giant. You can take it to a sage and have him perform some sort of divination to tell you what's in the box. You can throw it off a cliff.
All you need to do, as the player, is tell the DM what you want to try. Then it's my job to tell you how plausible your idea is, and warn you of any potential consequences so you can make an informed decision.
If you EVER feel like I'm not giving you enough information to make an informed decision, ASK ME FOR MORE DETAILS!
Be creative. It's D&D. Don't forget that.
And I swear, if you guys find a lockbox and the first thing someone says is a variation of "Hey guys, who's got the highest Thievery skill?" I'll punch you in the dick.