1. Think of the easiest taildragger you've flown and then think about something even easier to fly than that. A Citabria or Decathlon is still getting it's tail up when the -8 is already airborne. The rudder has excellent and very responsive authority even at low speeds. Citabria's are heavy, cluncky and non-responsive by comparison. On landing, the -8 is light on the touch, wants to wheel land (they tend to be nose heavy), but you do need to pay attention as the tailwheel touches down. I suggest letting it drop of its own will (keep the stick forward until the tailwheel touches) -- that way you're slow and it transitions easily. If you force the tailwheel down too soon it will give you a workout.
2. The new -8 kits don't use jigs. They are pre-punched and match-hole, you lucky dog.
I have a -4 not an -8, but they have similar characteristics and will depend on the individual installation (tail heavy increases the degree of difficulty).
I was a minimum time TW pilot before checking out in my -4 (180hp/CS). I soloed in a Champ, got about 7hrs of 170 time a couple years later and about 10 landings in an RV4 of a friend of mine. For me the 170 was by far the most workload, lot's of foot work to keep it in the center.
The transition to my -4 was a complete non-event. For me the issues were not TW related but high performance related. Dealing with the speed (inability to slow down really) and rate of climb were very different. You can be doing 160mph on downwind if your mind works at C172 speeds. After a couple of long orientation flights with my TW instructor he set me loose.
If you can get time in your local TW trainer and then hire one of the RV transition specialists and you will be fine, I can't think of an AC I've seen at an FBO that compares to an RV other than maybe a Pitts
