1938 Oldsmobile- Quarter Vent Latch Assembly

[cron1984]

Good evening,

I think this is probably straight forward but wanted to triple check as I may only have one shot to get it right. 
Got some parts back from chrome and I need to reassemble the latch handle to the rear quarter vent. I’ll ask my questions with the pictures as a reference. 
- Would the retaining pin go in knurled end first or smooth end first?

- should the pin go in from “front” to “rear” or the opposite?

- Any tips on best practices with regards to tools used, lubricants, etc would be much appreciated. Thanks you for your input.