[ImTellinTim]

Since I knew what was coming, on my 2nd playthrough attempt, my rule was I cleared out each segment of the map before going on in the story to a new segment. As I was going around for the uncharted chests and animus pieces, I attacked anything that was carrying metal. That always ensured that I had money and resources for upgrades, and it never felt like I was grinding.

It also helped that the ships and Kenway's Fleet cities I had cleared in my other save carried over. I started out with access to lucrative trade routes right off the bat.