About three weeks ago I started my tailwheel training. I'm flying a Supercub (well, 3 Supercubs) out of KCHD with the same flight school that has done most of my other ratings. I started documenting this on a less active forum, but I figured there are more people like myself here that can learn and appreciate this journey. I'm going to copy and paste some of my posts from there and add more as I get them 
For reference, I'm a CFI/CFII also with my commercial multi. Slightly less than 500 hours TT.
3/4/15
I've had 2 lessons in the Supercub so far. The first was a little overwhelming but the second, today, was amazingly fun. It's amazing for me to look back on this journey and think just three years ago I was practicing the same things, but in a Piper Warrior. And I needed to practice them a whole lot more!
We discovered upon entering slow flight that the flaps weren't working right. They wouldn't stay down for anything so we cut the lesson a bit short and just did two landings after airwork. One simulated emergency onto a dirt strip (wheel landing) and the other a 3 point back home. My 3 point wasn't bad! I'm sure I had a lot of help but things aren't so crazy and new anymore.
I also had an IPC today in the Skylane. It was a little weird coming from something with no vacuum system and 1 radio to my beautifully equipped Skylane. Felt like home though
Looking forward to this adventure.... I'd guess about 10-12 hours considering I'm doing it at a school known for its tailwheel and acro training and my feet aren't the fastest. But I know I'll learn more here than just about anywhere else which is why I chose this school for my private (and beyond) in the first place.
For reference, I'm a CFI/CFII also with my commercial multi. Slightly less than 500 hours TT.
3/4/15
I've had 2 lessons in the Supercub so far. The first was a little overwhelming but the second, today, was amazingly fun. It's amazing for me to look back on this journey and think just three years ago I was practicing the same things, but in a Piper Warrior. And I needed to practice them a whole lot more!
We discovered upon entering slow flight that the flaps weren't working right. They wouldn't stay down for anything so we cut the lesson a bit short and just did two landings after airwork. One simulated emergency onto a dirt strip (wheel landing) and the other a 3 point back home. My 3 point wasn't bad! I'm sure I had a lot of help but things aren't so crazy and new anymore.
I also had an IPC today in the Skylane. It was a little weird coming from something with no vacuum system and 1 radio to my beautifully equipped Skylane. Felt like home though
Looking forward to this adventure.... I'd guess about 10-12 hours considering I'm doing it at a school known for its tailwheel and acro training and my feet aren't the fastest. But I know I'll learn more here than just about anywhere else which is why I chose this school for my private (and beyond) in the first place.
Unlike a tricycle, with conventional gear you want to 'drive it on'. I find them easiest just trim for the landing speed then just use the throttle to get the wheels down to the runway with minimal pitch inputs. Once you get used to them though, they are what provide one of the big benefits to tailwheels, you have a much larger envelope of landing speeds.