Tigerdude,
Just like everything else in the hobby drilling bolt holes takes a little bit of practice, but it's not hard at all to do. It's well worth it to learn how to do it if you plan on staying in the hobby. The reason I say that is that rubber-banding a wing is a bit frustrating as you advance in the hobby. I'm not talking about the physical act of putting the rubber-bands on, but what I'm referring to is that fact that it is next to impossible to have consistent wing placement each time you assemble your plane at the field. Even if you have alignment marks for placing the wing it's still pretty easy to have the wing a tad bit out of "skew" when you put it on. Plus bumping the wing can knock it out too. This leads to having to re-trim the plane every trip to the field. While this may not be an issue in a trainer, or even a second plane, but when you start getting into more advanced planes it's really becomes an issue. Especially when you start trying to improve your skills and practicing maneuvers, having the wing in different positions can make a plane handle a bit differently each time.

Recovering from an improperly drilled hole isn't really that difficult. Usually the place where mistakes happen is when you drill the bolt holes in the fuselage and then tap the hole to put threads in it. Those are really easy to fix if they are messed up. Just drill out the hole larger than it was and epoxy dowel into the hole, and then try again. Usually you can get it all drilled properly if you do it all at once. What I mean by that is to position the wing and make sure that it's aligned on the fuselage, then mark where you're going to drill, and then drill all the way through the wing and the bolt plate in the fuselage. That's usually the same method that most instructions in kits will recommend too.

Hope this helps

Ken