Carl,
Don't have any data to support this, but it seems that I see a number of accidents involving the combination of a new tailwheel pilot checking out to fly tailwheel while also doing the first few flights of a tailwheel conversion airplane or homebuilt.
My suggestion would be to get a tailwheel checkout in something - a converted 150 if available or 140 or 120 or 170 so that you have established that gut feeling for how an airplane behaves on the ground when the c.g. is behind the main landing gear. Get that over with before your airplane is done.
Then, either have an experienced tailwheel pilot make the first few flights in your airplane - someone who can tell if the fact that it is weaving along on the ground in a moderate speed taxi is due to a tracking problem with the gear versus skill level of the pilot. Then you fly it with an instructor. There will be differences in behavior between what you got your checkout in, but those differences will be relatively minor because you have already made the big leap to tailwheel operations.
I found that even though I had well over a thousand hours of tailwheel time, that when I checked out to tow gliders in a tailwheel 180 hp Cessna 150, it was challenging. That particular airplane had very spongy gear that wasn't aligned quite right and it would rock in one direction and dart in another - really tried to fake you out on landing. I would not like to have taken my initial tailwheel training in that airplane, just converting to it and getting comfortable was challenging enough.
Best regards,
Rick
