Peggy Loeffler is an FAA-Designated Pilot Examiner based out of the Great barrington, Massachusetts (EA63). View Peggy's profile and request a checkride today.
I don't know if he'll do a TW checkride or not, but Robert Dumovic has a lot of tailwheel experience (and is there something up with DPEs in MA? I just searched directly through the FAA site, and most of the names I expected to see don't show up)
The DPE isn't giving instruction, he's riding with someone who has been trained and is demonstrating his abilities. The applicant is proving to the DPE that he is capable of performing as a private pilot. The candidate shouldn't have to train to the DPE's comfort level. If the DPE isn't comfortable riding in a certain type of airplane, he isn't qualified to be a DPE in that type of airplane. This is why a DPE has specific muti-engine airplanes on his authorization. If the DPE is touching the controls he is either instructing or failing the applicant or both.