Its not really a grind when you start to understand what kind of gear you need for your bros to actually become effective murderfuckers. There is a couple of things you need to do to turn your bunch of retards into semi-working war machine and after you level them up or hire some better dudes enemies like bandit raiders become laughable loot piniatas that barely even scratch you.
The most important thing is to get heather shields, I cant stress this enough, they turn even the biggest retard into unhittable Neo with shield wall, every city and keep you go through make sure to get those from the armoursmith. Second thing you should care about is getting some decent weapon composition. Spears are shit except when fighting monsters or your bro is half blind and has 40 melee skill, from my experience Bandit Raiders very often have flails with them, which are excellent weapon for your every decently melee skilled bro, every fight you have 2-3 morons that forgot their hats that you can instagib with flails, that nets you their armour for free from the get go. Flails also go around enemy shields which are pain in the ass in the beggining, so although they dont have any to hit chance bonus, they dont get the enemy shield malus so its pretty much the same as using a spear, except you actually deal some damage. Flails and hammers also deal the best debuffs in the game.
Dont split shields unless you know you are going to kill the guy this round, otherwise instead of cowering behind his shitty wooden board he will get the two handed grip damage bonus and go berserk at your dudes.
Backstabber and crippling blows are AWESOME for your bros with reach in the second row, you usually level up bros with pikes or longaxes or even pitchforks, with backstabber position them on flanks and they easily turn the tide of battle. Just dont give backstabber to guys you know are going to be front line after leveling, but for sarge or dedicated billman its awesome.
Now, getting armour is the difficult part, you really want to have some chainmail by day 5 or something like that so you can actually do every contract instead of phishing for easy, barely paying jobs.
Consider having a specialist stun-bro with some mace early on when you have no armour so you can stun the enemy you want to peel from armour, its even good to give that stupid mace to one of your most accurate bros so you can reliably stun your target. Now, you NEED to have a dagger or at least a knife on everyone, they dont cost any stamina to wear so when you see an opportune target to steal items from you just knife the motherfucker to death while surrounding him for maximum flanking bonus. Bandit leaders become a walking pinatas of loot if you block them with your best tank, they always start behind their dudes so before they enter the fight usually a couple of enemies are dead, then you just whack 2-3 more dudes, start a rout, and surround poor leader with your knifebros.
The only problem I constantly have is to actually find competent recruits, its stupid that you have no idea what your recruit can do besides his background and name title they sometimes have. Trying to find a competent duelist candidate is such a pain in the ass I've never actually fielded one.