Hey Guys, basically, you can cross Blackwater as Arthur completely Unhurt as I did in the video. So every journey from Saint Denis to New Austin counts (at least you don't die in Blackwater)

Please watch till the end and follow what I do. In the video, the spawning Pinkerton locations I point out are 99% accurate.

Tall Tree entrance (I did) is nearer for Middle and North New Austin.
Thieves Landing entrance is nearer for Middle and South New Austin.
The wooden bridge (middle) may be the easiest to enter.

I have got many videos about how Arthur Explores and Collect Items in New Austin. Please check them out, too.

Hope it can help you. Any questions, please leave a comment.