Get to know the specific aeroplane - fly that one, not some generic taildragger! Some prefer wheelers, some 3-pointers, some are ambivalent.
Whilst I agree with that this is someone that does not know how to wheel on so I would say yes, go and learn how to do it, but make sure the aircraft is suitable for learning that, also, when you then go and fly a new tailwheel type learn the specific advice for that type.
Quite a good example is our RV7, wheels on nicely - as long as the tyres are fully inflated, if they are not then it really does not want to know!