The one I built yesterday was done in haste.
I have a set of punches specifically for the smithing box on a truck headed this way, but couldnt wait.
What i did have was a framing hammer... a dremmel cut off tool mandrel, and about a 3/8" o.d. x 5" long clevice pin with a nice square end.
And the corner of a crafts working bench I built for the Wife... (leather, wood burning, carving, sculpting, etc.. and so on)
The only roll pin that gave me any guff was the trigger guard roll pin like you are having the issue with...
I supported the "ears" on a corner of the bench... held steady and positioned the lil dremmel mandrel with my left hand and kept trying to set the pin in the hole with little taps trying to be careful...
Not so much...
Smack that sucker in there. Once it starts the stress level drops and it goes the rest of the way pretty easy.
Congrats on the first lower!
Between this and modifying my truck im gonna go broke lol