With some 250 hours on DH84 and DH89A types in the dim and distant past I may be able to shed some light on the queries.
Conversion to type was done once the individual had already obtained his multi-engine piston rating. He or she would have plenty of tail wheel experience along with a reasonable amount of time in vintage biplanes such as the Tiger Moth. Experience on the Leopard, Puss and Hornet Moths would have been beneficial since both the Dragon and the Rapide had similar braking systems.
With the "student" and the "instructor" as the sole occupants plus a good load of ballast on the rear seats to keep the CofG nicely inside the envelope the " instructor" would fly the aircraft to demonstrate a flight including general handling and stalling plus a bit of asymmetric flight, a demonstration of the asymmetric committal height along with the takeoff, a few touch and go's and a full stop landing. For this session the "student" would be in the front right hand passenger seat in order to listen and observe.
Following a comprehensive debrief the "instructor" would again take off and clear the area climbing, if possible, to above 3,000 feet. He would then trim out carefully and ease his way out of the only pilots seat into the cabin. The "student" would then be able to slide through into the vacant seat. With the "instructor" observing and making pertinant comments the "student" would carry out his own evaluation of the handling characteristics and performance under symmetric and asymmetric power settings. When both pilots were happy then a rejoin would be flown leading to a few touch and go's including missed approaches and simulated single engined circuits. Finally a few full stop landings would finish the detail.
Again a full and comprehensive debrief would consolidate the flight and settle any queries.
If both pilots were happy then the first solo on type would follow this, again followed by a good debrief.
The newly converted pilot would need a bit of close supervision until a reasonable number of hours had been achieved.
Later on a similar "dual"/"solo" session would be needed to cover cross wind techniques, hard runway operation and short field landings.
As the pilot gained experience then the load could be increased up to the MTOM where the reduction in performance is quite marked.
Cheers,
Trapper 69
PS - In my own case having done my multi-engine rating on a Cirrus Minor powered Miles Gemini in some six hours my very next flight was as PI in a Rapide G-AKNN accompanied by eight parachutists. 15 minutes later I landed on my own. They knew it was my first landing on type and preferred to go for help on the ground should it be necessary...........!! Oh thee of little faith.
PPS - Getting the tail up too early in the Rapide or any tailwheel type can aggravate the swing due to all the pro-swing factors coming virtually together. If you wait until there is a bit of airflow over the fin and rudder the aircraft is much easier to control in yaw as the tail rises with forward elevator. Hope that makes it clear.