With enough time in the boat, you should develop a feel for almost anything that you might encounter. However, this might take a good long time and lots of situations that might not come up very often I once had a canoe that I thought was the most unstable boat ever invented. I’m not exaggerating–it would capsize if I looked up at a bird. I know now that the bird had nothing to do with it; it was just me being too rigid and not yet having any confidence in the boat.
Even with the boats I have now, there were a few times when I didn’t feel very secure. All of that is gone now, because I’ve purposely put myself in conditions that a few years ago would have had me ready for a swim. Sure, there are things that can get a little daunting now and then, but the key is trusting the boat and staying completely loose.
I really don’t think that having a skirt on is going to do anything, but give you a bit more confidence. While you’re fishing, my concern about having a skirt on, would be getting a hook anywhere close to that skirt.