I recently made an oiling mistake:
You can see how the rind has got bumps on it (like pimples, kind of). This was apparently due to oiling too early.
Last night I was reading old postings here on the topic and the long and the short of it is that if you oil too early, you've got a good chance of yeast getting driven into the rind. It stirs the rind up like that and you end up with lots of crevices that blue loves (you can see a bit of blue in that picture). What you are supposed to do is to age it 2-3 weeks as normal, wash it, dry it and then oil it. I've done that before and it's worked well.
Mainly an oiled rind is there to keep the moisture in the cheese, not to combat mold. This was something I kind of new, but hadn't thought through. Basically, if you bring your rind through the 3 first weeks, it's basically easy after that anyway. Once the rind is established, you can kind of ignore it. In my last tomme, I ended up washing it (for reasons) and then I got a great bloom of mycodore with a nice rosy rind from a little bit of b. linens. It was awesome. But you can also just let it grow blue and it doesn't matter (done that many times too). An oiled rind build up a nice slick surface eventually, but it's actually too late to help you with the difficult part of the mold.
The other thing I didn't understand about oiling is that you want only enough that it is absorbed by the rind. If there is any greasiness left on the rind, then there is a good chance it will go rancid (olive oil is less likely to do that, so it's worth the cost to use it).
Anyway, that's my Colby style cheese I did about 3 1/2 weeks ago. It worked out really, really well! Definitely going to use that recipe again. I based it half on a video of a factory producing Colby and half on one of Mal's old recipes. I just needed to let it acidify a *bit* longer and a bit more age would have been good.