It is important for tricycle pilots to realize that training in a tricycle does not prepare one for being adequately skilled to land a taildragger. That is separate training, and needs to be taken. Who would think to take their 100 hours in a 172 wheel plane, and jump into a 172 floatplane and go for a circuit with no training on floats? Cessna did not call tricycles "Land-O-Matic" for nothing, they are more forgiving of poor technique. Thus, taildraggers require more, or at least different skills.
A very current experienced pilot might be able to be talked through checking themselves out in a taildragger, if the mentor were effective. If you fly a taildragger with precision and skill, they are not more difficult than a tricycle. But, I observe that many of today's pilots have not been trained to fly with that amount of precision - thus they should expect a taildragger to challenge them.
Ultimately, a taildragger will provide you with greater landing capability, in trade for less tolerance of sloppy technique. I have not known a tricycle only pilot who was easily able to transition to taildragger with only a couple of hours [in a Cub]. Yes, they could fly it, but during a landing, they were at the edge of their skills before they were at the edge of the aircraft's capabilities.