Hallo hruza,
I just saw right now, that there is a second page on which your advice regarding challenges is located.
The first challenge I always pick is befriend a settlement. After that comes either hire 12 brothers or get 2000 crowns for a standard. Later on I do the sergeant quest, because a sergeant is needed in the band anyway. Increased inventory space is also nice after the first challenges. The trophy challenges I did do rather late, at least I did in my beginner playthrough. But it is nice to know that I did not to much wrong in this section of the game.
Maybe I just have to start a beginner run again to try out all those tips. As it stands now I just get horribly beaten on veteran despite changed approaches and okay tactics. (At least my tactic looks okay when I compare it to the playthroughs I have watched on youtube.)
Best regards,
Taito
