There is a number of skulls above the contract that gives you basic idea about it’s difficulty. I imagine this contract had 3 skulls above. Playing on deadly you need to be picky with contracts at first, try going for 1 skull contracts, avoid protecting village from “terror” before having a decent front line. I also did some research and killing Hoggard on deadly is way better then skipping this mission. (I had about 15 restarts already). I traded only once when the location was very beneficial (plenty of towns with trading goods in 3 various locations accessible from ports and a huge harbor to sell goods to) and once I’ve got some lucky patrol marching ahead of me and a few kills bouncing my way so I had great equipment. Other then these 2 cases I managed to go by with initial 1400. Killing Hoggard is easy because there are no raiders with him, just thugs.