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A 'training flight' implies the instructor acting in his normal capacity and so the flight is dual with the FI as captain. If that's the case then the FI would need to be qualified to act as PIC.
Question is: Does the flight have to be the "entire flight" incl take off & landing or can the training start & end at pre-arranged points? Bearing in mind the "student" is still qualified to be PIC at this time <30 June.
It may be a question of "a flight" is considered just that, brakes off to brakes on.
If this is the case then all us taildraggers have to either find a taildragger instructor who are few & far between here, or spend lotsamoney on a flight in an a/c that is no longer current. Pushing forward on the yoke during takeoff might not go down too well!!