I think you should go to Vid's big flipper rebuild thread, it will be better. I posted my flipper rebuild questions there and Vid got answers for me right away. I will be interested in the answer since I am headed for a rebuild soon. But, I can tell you that I have hammered in those things before for other projects and yes they are a pain. It is a matter of holding firmly it in just the right position to get it started.
First, I generally try to leave them in and only back them out enough to get the pawl out. I think now you know why.
Regarding getting the roll pin back in: If you have a drill press or an arbor press, it is easier. Put something that is roughly the size of the distance between the upper and lower plate in the pawl to support it and keep it from bending in. Compress the roll pin slightly with a vise grips, squeezing at 90 degrees to the slot. Position the roll pin over the hole and press it in just enough still allow the insertion of the plunger and link assembly. Remove the support and put in the plunger/link assembly. Support the plate with the blade of a screwdriver and press it the rest of the way in.
If you don't have a press, you can still do it with that hammer there, it's just a little tougher to line things up and if somebody calls you a sledgehammer mechanic, well... you earned it. (seriously, though, it is fine)
I just squeeze it with needle nose and position it right above the hole at a 90-degree angle to the slot, as described above. Then I usually use a nail-set (punch) and use that to tap it into the hole. I usually rest the arm on a wooden sawhorse and just tap it in while resting on there. They do take patience, but you can do this.
I made a tool from a bike chain tool.
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