Just take a vanguard, load it up with 4 other people, outfit everyone with claymores and vanguards, and pray that luck is on your side...cause you could get unlucky and get hit a 45, 45, and 10...
2. Fire the crew member with weak attack/defend skill. Just go to new cities and take the best fighting dudes. Pick up poor men during the way and see if they are good. If not, fire them instantly.
I had my own character (weak on combat skills but you can't replace him) and dudes with minimum skill levels 3/4 and 4/4. There are some who posses 4/4 on both defense and attack but they seem to be rare. I had only one. Nevermind the other skills cause you have enough money already.
Repeat this until ready to kick some butt.
3. Have the most powerful weaponry.
4. If the first two attacks aren't dealing damage more than let's say 75 points you should surrender. Also pay attention to your health on the 3rd attack cause if you are low on health it's risky. However the situations may vary so you should experiment.
5. Always have at least 2000 in cash with you. You may get robbed...
buy a vanguard. get the best people that have good defense, and attack. it doesn't matter what their travel and trade is. got to a city. try not to get hurt on the way there. get to the city, and hit battle. fight and fight. don't die.