Flown a Taildragger
Pilot DAR
The reason why I believe that some upper air work is necessary is straight forward enough.
If a student is undergoing a tailwheel conversion then by definition they will not have piloted that type of aircraft previously. Therefore they will not be familiar with the individual handling characteristics of the aircraft and as such some familiarisation of steep turns and stalls would be beneficial. I think you would agree that in the early stages of learning to land a tailwheel aircraft, mistakes will be made and the old adage of ' if in doubt, go around' is vital. As such some practice of go around handling in various configurations will give both student and instructor confidence before going on to the process of landing the aircraft whichever technique is taught first.
Regarding the sideslip, I have found that it is a technique that is not taught well at PPL level neither is it practiced. It is quite possible to mishandle a sideslip approach, particularly the transition phase, so why not give the student the opportunity to look at the manoeuvre with some altitude to play with below.
I thoroughly agree that the Wheeler landing is under-rated as a technique - some tail wheel pilots are obsessed with the three-pointer despite all the variables that may make it very much the less favourable option.
Obviously every student is different both in terms of experience and capability. It is our job as instructors to formulate a training plan accordingly which covers all the relevant aspects of tailwheel training.
The reason why I believe that some upper air work is necessary is straight forward enough.
If a student is undergoing a tailwheel conversion then by definition they will not have piloted that type of aircraft previously. Therefore they will not be familiar with the individual handling characteristics of the aircraft and as such some familiarisation of steep turns and stalls would be beneficial. I think you would agree that in the early stages of learning to land a tailwheel aircraft, mistakes will be made and the old adage of ' if in doubt, go around' is vital. As such some practice of go around handling in various configurations will give both student and instructor confidence before going on to the process of landing the aircraft whichever technique is taught first.
Regarding the sideslip, I have found that it is a technique that is not taught well at PPL level neither is it practiced. It is quite possible to mishandle a sideslip approach, particularly the transition phase, so why not give the student the opportunity to look at the manoeuvre with some altitude to play with below.
I thoroughly agree that the Wheeler landing is under-rated as a technique - some tail wheel pilots are obsessed with the three-pointer despite all the variables that may make it very much the less favourable option.
Obviously every student is different both in terms of experience and capability. It is our job as instructors to formulate a training plan accordingly which covers all the relevant aspects of tailwheel training.
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I certainly agree that if a student is so unfamiliar with a type that upper airwork is justified, than of course, training should never be skipped. If it's the student's first time flying stick, then yes...
As for sideslips, the reality that it is poorly taught is sad, and no excuse. Many taildraggers will require a sideslip to refine all but the most well set up approach. I have never found a type which will not respond well to being slipped, right up to full rudder. The King Air 200 has some odd tendencies, and its type certificate has a special condition in that regard, but an attentive pilot should have no problem. As for any other type, certainly, the student should be taught, then allowed to practice at altitude. Thereafter, as an element of tailwheel training, a sideslip just into the flare should not be concerning. I do not view a sideslip as a risky maneuver in the sense of approach to stall, as the whole point of the sideslip is to create drag to reduce speed, so if you're anywhere near stall speed, entering a sideslip would be pointless unless you're silly high. FWIW, in negotiating with Transport Canada Flight Test staff last December to not have to demonstrate spins in a modified Cessna Grand Caravan, I accepted instead demonstrating stall to the break with 75% power, in a 30 degree bank turn both ways, with one ball out (which was just about full rudder) - so a horrible sideslip, approach to stall. The stall was very benign, as has been my experience testing other smaller types this way.
I have never flown a Pitts, so would defer to those which that experience for their opinion on technique. I agree the the Tiger Moth seems to like either landing technique (or doesn't know the difference!). That said, I've never been formally type trained in the Moth, I just checked myself out when it needed to be test flown post maintenance. Again, I would defer to Tiger Moth experts for the best technique.
But, for the number of worn out tailwheels I have repaired from Cessna 180/185's, PA-18, the 172, and my flying boat, I choose to hold the tailwheel off as long as I can to reduce wear and tear - thus wheel landings. For bounce arresting, once I have both mains planted, I'll lift the tail. The loss of AoA on the wing pretty well assures that it's not going to fly again, so no bounce into the air 'cause it's still flying. If I've hit so hard that it bounces on pure landing gear spring, well, that's pretty embarrassing!
When landing skis in unbroken snow, it is normal to hold the tail off to assure that you have not committed to a landing until you're happy with the snow. If you three point into snow, you may just drop and stop if the snow is deep or crusty. Done that way, you may be calling for many friends with shovels - I've known it to happen! So I'll put one ski down first (usually the left, if the wind permits), and watch and feel what it does, before I even allow the right main to go down, let alone the tail. If the snow is too deep or crusty, and the plane pulls, I'll put on the power and go around, it was flying the whole time. When I was testing the 150HP C150 taildragger on wheel skis, I deliberately landed three point into snow (beside the runway) which I knew to be 18" of loose powder. Snow flew everywhere! Takeoff was not possible, just too much drag, and that was what I expected. I snowstormed out to the runway, and took off on wheels. It has been known that the tail post has been pulled out of PA-18's and Maules on skis, when the plane was three pointed into crusty snow. For landing on very soft grass or sand on tundra tires, I employed the same left wheel first and feel technique, and a few times it saved me from getting stuck, as I felt it pull, and rapidly did a go around. The Tiger Moth I flew on skis had the "Canadian" main landing gear, which was canted forward at a greater angle, to reduce noseovers on skis.
When I was trained in the Turbine DC-3, three points landings were a no no under any circumstances.
So I listen to what the type expert tells me on any given type, and defer to a wheel landing if I have not received any advice.
As for sideslips, the reality that it is poorly taught is sad, and no excuse. Many taildraggers will require a sideslip to refine all but the most well set up approach. I have never found a type which will not respond well to being slipped, right up to full rudder. The King Air 200 has some odd tendencies, and its type certificate has a special condition in that regard, but an attentive pilot should have no problem. As for any other type, certainly, the student should be taught, then allowed to practice at altitude. Thereafter, as an element of tailwheel training, a sideslip just into the flare should not be concerning. I do not view a sideslip as a risky maneuver in the sense of approach to stall, as the whole point of the sideslip is to create drag to reduce speed, so if you're anywhere near stall speed, entering a sideslip would be pointless unless you're silly high. FWIW, in negotiating with Transport Canada Flight Test staff last December to not have to demonstrate spins in a modified Cessna Grand Caravan, I accepted instead demonstrating stall to the break with 75% power, in a 30 degree bank turn both ways, with one ball out (which was just about full rudder) - so a horrible sideslip, approach to stall. The stall was very benign, as has been my experience testing other smaller types this way.
I have never flown a Pitts, so would defer to those which that experience for their opinion on technique. I agree the the Tiger Moth seems to like either landing technique (or doesn't know the difference!). That said, I've never been formally type trained in the Moth, I just checked myself out when it needed to be test flown post maintenance. Again, I would defer to Tiger Moth experts for the best technique.
But, for the number of worn out tailwheels I have repaired from Cessna 180/185's, PA-18, the 172, and my flying boat, I choose to hold the tailwheel off as long as I can to reduce wear and tear - thus wheel landings. For bounce arresting, once I have both mains planted, I'll lift the tail. The loss of AoA on the wing pretty well assures that it's not going to fly again, so no bounce into the air 'cause it's still flying. If I've hit so hard that it bounces on pure landing gear spring, well, that's pretty embarrassing!
When landing skis in unbroken snow, it is normal to hold the tail off to assure that you have not committed to a landing until you're happy with the snow. If you three point into snow, you may just drop and stop if the snow is deep or crusty. Done that way, you may be calling for many friends with shovels - I've known it to happen! So I'll put one ski down first (usually the left, if the wind permits), and watch and feel what it does, before I even allow the right main to go down, let alone the tail. If the snow is too deep or crusty, and the plane pulls, I'll put on the power and go around, it was flying the whole time. When I was testing the 150HP C150 taildragger on wheel skis, I deliberately landed three point into snow (beside the runway) which I knew to be 18" of loose powder. Snow flew everywhere! Takeoff was not possible, just too much drag, and that was what I expected. I snowstormed out to the runway, and took off on wheels. It has been known that the tail post has been pulled out of PA-18's and Maules on skis, when the plane was three pointed into crusty snow. For landing on very soft grass or sand on tundra tires, I employed the same left wheel first and feel technique, and a few times it saved me from getting stuck, as I felt it pull, and rapidly did a go around. The Tiger Moth I flew on skis had the "Canadian" main landing gear, which was canted forward at a greater angle, to reduce noseovers on skis.
When I was trained in the Turbine DC-3, three points landings were a no no under any circumstances.
So I listen to what the type expert tells me on any given type, and defer to a wheel landing if I have not received any advice.
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Pilot DAR. Interesting view on wheelers versus three point landings. Not sure I agree (actually i am sure, I don't agree). Both techniques have their place and you can use either, to your prefence, in many situations. However, a tailwheel pilot should be proficient in both as sometimes only one of them will do. For what its worth, for the lighter (and more vintage) aeroplane I suggest that 'proper' pilots have always landed on three points. 
Your suggestion that wheelers are less prone to bouncing also does not chime fully with my experience. Depending upon the undercarriage arrangement, wheelers can be more prone to bouncing than three pointers, e.g. in a Tiger Moth. On the other hand a Pitts is probably more likely to bounce during a less than perfect three pointer than during a wheeler.
Your suggestion that wheelers are less prone to bouncing also does not chime fully with my experience. Depending upon the undercarriage arrangement, wheelers can be more prone to bouncing than three pointers, e.g. in a Tiger Moth. On the other hand a Pitts is probably more likely to bounce during a less than perfect three pointer than during a wheeler.
Harvards, Stearman, Cessna 195s are also vintage but are heavyweights in their own right.
Wheelers or 3 points, this discussion is as old as the hills. There are so many dependent factors - type of a/c, loading, length of runway, hard or grass, wet or dry, crosswind, headwind, no wind, the list goes on.
It’s largely down to ability, experience and currency. Personal preference comes in to it a little bit but not much, more so with experience.
Aerodynamics dictate that a wheeler landing means that whilst the tailwheel is in the air and the aircraft is running along on its mains then the wings are developing lift, any rearward movement on the stick is likely to make the aircraft fly again, even if it’s slowing down. The most important thing is to keep feeding the stick forward until the tailwheel touches, try to keep the tailwheel in the air, full forward stick. Once the tailwheel is down the stick can come briskly back.
On the other hand, the aim of a 3 pointer is to land on all 3 wheels, stick hard back and at, or very slightly above, stall speed.
Too fast will result in a bounce and flying again.
Too slow and the a/c will stall above the ground resulting in a sharp drop and a heavy landing (not very graceful).
Both can be corrected with a trickle of power at exactly the right moment. Resist a PIO at all costs, if there is any sign of that, any doubt, power on and go round. Remember that powering up will lower the stall speed and you’ll be flying again, at your landing speed, just above the ground, let the speed build up then climb away.
A pilot, with a bit of experience, will be able to turn a slightly fast 3 pointer into a bit of a tail low wheeler, could be an embarrassment saver.
My personal rules of thumb are:
Tarmac - always a wheeler, runways are generally smooth, you can land at high speed and are better equipped to deal with crosswinds control wise.
Grass - you have a choice, unless it’s a short runway, if that’s the case then ‘drag it in’ as slow as is comfortable and 3 point it.
With all of that said, you won’t be wheeling a Tiger on to a hard runway if it’s got a skid, which goes back to my earlier comment regarding type of aircraft.
And then there’s tarmac crosswinds, that’s a whole different story.
A quick word about ground looping. Once again it’s a physics thing. On a tricycle the CofG is ahead of the main gear - natural tendency to track straight.
On a tailwheel the CofG is behind the main gear - prone to shopping trolley behaviour. Try pushing your wheeled carry on luggage at running speed, you’ll get the idea.
Before I get shot down, I speak as a current taildragging pilot, over 3 decades and multi thousand hours, from Cubs to warbirds.
People may not agree with the above but they are my personal views based on my own experiences.
I've never flown a DC3 but, I've been told (and as Pilot DAR says) you DON'T three point them, also with Dragon Rapides. Conversely a tailwheel Eurofox is happier on three points.
I suppose we could go on...
