Now that I checked the threads are maxed out, post is all the way thru, put a washer under the nut but threads on nut not so good, probably didn't help trying to screw past the end of threads on the inner wedge or 87 yrs of ware ( was only used for 1 yr so who knows ), swapped to out to the other unit with better threads and a washer and seems better, didn't want to tighten to much till I get better washers and then I'll experiment a little more.
Mark.. Here's some measurements from mine.....
Seat tube OD...
Bushing head OD...
Amount of threads on mine (and it's tight), also gap measurement.
Questions.....
Does your bushing drop in easily, or do you have to force it in & out?
What is the OD & ID of your seat tube?
Does your wedge still have this profile, or does it look like it was ground down?
One of the things I noticed in your pic here is that the wedge is way up in there, and it shouldn't do that...Like your wedge isn't a wedge.
If your tube OD is larger than mine, that could be the issue. If the opening is too large you can do a couple of things..
One is to make some brass bushings like these to go around the bushing to decrease the dia. of the seat tube, and or do the same where the wedge goes into the bushing.

Since you have them out, I would put the seat tube bushing in a vice and squeeze it down to the ID of your seat tube, put the nut on the post, slip it thru the bushing, put the wedge on with the seatpost out at least 1/8" and shove the wedge in and see how for it goes. If you have more threads than what I show in picture of mine before tightening, I would go the brass insert route to decrease the tube ID. That way you won't damage the nut or threads anymore... I have some extra brass sheets laying around and would more than willing to make you some to try...
Also, for those that aren't familiar with these, I made this little cutaway drawing to show.. They are quite simple when you've messed with them.