What level would you guys recommend I jump into the DLC at? I started a new character to play it since my main was in NG+.
lvl65 is what is recommended by the devs and IMO it is pretty decent place to start. You can go there earlier and try how it goes but it will be tough.
In comparison to the bosses before it, without giving me much information, how hard is the boss in Fishing Hamlet?
Hardest boss in the game for me.