OK IMA confirmed via email that we are all correct - fat part of the insert goes towards rider to reduce the offset. Enshrining this here for future passers by.
IMA adds an extra locking nut on the top side so that the steering stem stays locked to the steering head at all times. This is meant to facilitate dropping the top and bottom triples independently of the steering stem and bearings, so that you can change out offsets relatively easily in the future.
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Also, these steering stops they send have to be adjusted just right on the bottom triple so they don't interfere with the steering on either side. Best to do this after everything is mounted so you can see where they rub and where they don't for adjustment.
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@endodoc thanks for the tip on the bearing. I didn't bother with tapered and just re-used my OE bearings since the bike has only 1500 miles on it and OE bearings are still good. More than anything, I didn't want to wait around for the bearings to arrive and dust seals are back ordered. If anyone did want to change out the bearings though, keep in mind that you can change out the entire "bush" (top and bottom races, bearings and dust seals are all encapsulated inside what Ducati calls a "bush" so instead of hammering out the races and hammering new races in, you can replace the entire bush unit as a package if you wanted - one bush up top and one at bottom FYI. You gotta buy two bushes, two bearings and two dust seals).