You obviously have good ears since you're flying a single engine tail dragger and you're still alive. I'm sure you've. had to land a few times just on the sound of the engine. You need some brass to fly those.
Tailwheels are not all that difficult to deal with if you pay attention (after initial training, that is). Where people really have problems is when they let their attention lapse, often relaxing before the aircraft comes to a stop, thus causing themselves problems. It doesn't take brass, just a willingness to pay attention to what you are doing -- as my first instructor said about landing, "Hold the aircraft six inches off the ground [ed: that's with power at idle] and keep it that way until you get to the tie downs, then pull it down that last six inches with the tiedown ropes." Of course what he really was saying is to keep flying the aircraft until you're stopped and shut down.
It's really no big deal if you pay attention instead of daydreaming.
I have a friend that is IFR certified; I hope he doesn't kill himself. My wife thinks a 60 million dollar 50 seat commercial jet is too small.
Once again, if he pays attention and uses good judgement, he'll do fine. It's dangerous mostly when you develop "get-there-itis" or otherwise use poor judgement (including exceeding your skill level), or when you let you skills deteriorate. Of course you need to pay special attention when the chance for ice or thunderstorms is there, but in that case staying on the ground for a little while is a good idea (with certain exceptions).
Given the above, it's not much more dangerous for a single engine aircraft to do IFR than it is for a jet airliner, but you do have to pay attention to certain additional limitations (yes, even giant airliners have limitations).
The biggest thing that causes fear of flying is a lack of understanding, coupled with its unfamiliarity and the fact that, to a ground pounder, it's far from intuitive. But a bit of learnin' can do wonders, IF the individual is willing to learn.
