I would suggest to put low level bros in the backline, with a reach weapon and to avoid any dangerous situation. Going from level 1 to 3 can give a lot in the way of survivability with like dodge, colossus, steel brow or whatever.

Once I'm satisfied with the survivability of my bro I use him in the intended way.

Active abilities are critical to reducing bro death rate. Things like stun, knock back, repel, footwork or rotation helps in overcoming bad rng rolls and save a brother that would be bound to die otherwise.

Other abilities like adrenaline won't allow to save a bro immediately, but having two turns worth of attack before the opponent moves rather than just one can be the difference between a smooth fight and having to go out of my way to save a bro.

After 4 wipes and a 5th resignation as the 'Noble War' outcome made my position hopeless, I think a lot of of the challenge is being an effective commander when the AI is pretty smart and the special units can be very spicy.

What I've discovered so far:
1) You really need at least a 5/7 backline. Reach weapons or Crossbows (Bows suck, don't use them). Concentrating fire will kill troops, and killing troops demoralizes as well as somewhat reduces damage you take in a fight.
2) There is nothing wrong with the Russian Conscript school of WalMarting your new soldiers. There is no concern about cannibalizing gear off of your dead dudes, and you can therefore hire people for low lumps and wages; if they make it, they have staying power, if they don't, no great loss.
3) Level Up really indicates what your soldiers are going to be good for: Someone who bumps Stamina and Melee Skill is going to be frontline; someone who is good at ranged targeting is going to be a good candidate for crossbow duty. This doesn't do much at the start of the game, when you're never going to pay 400 GP for kit someone brings with them, and you can begin the replace and enhance model.
4) You can pick impossible ambitions. Stockpiling money is always doable; beating another Mercenary Company, well, better already have the best stuff in the game before you try it. This is realistic if kind of nasty game design.
5) Caravan missions are bad--only do them if you know the route is clear, in which case its a paid walk. Armed Courier missions, given that you can generally break away from overworld encounters, are fight optional payments. Most are going to be fight one encounter and get paid.
6) If you can buy a trade good under cost, you will make a profit. It can be very profitable to get in good with a city that sells it, as relationship bonuses can lower the price further, and remove negative circumstances that drive up the cost.
7) You will generally never regret taking on 'too easy' of a mission. It will build relationships, things you fight will have loot you can sell. There are no controls, however, to avoid a wipe on a bad mission, so, never accept Caravan missions unless it's clear and be extremely careful when considering a harder mission.
8) I find that, aside from being put in a hopeless position, the biggest weakness you can have in this game is pride. I have repeatedly come to grief by taking jobs I've shouldn't, fighting things with advantages over myself, or facing superior foes. What this game will teach you, is how to say NO to reckless and suicidal risks. Your men need to be bold, stubborn and ready to trade one more blow; your lot is to be shrewd.
9) No one ever punishes you for asking for more money. Try it.

You need to protect your new bro until he can level up. That's it.
And you should take more than passive abilities to increase your options in combat.

As for threeist views, my take on this is
1. You can have a full Frontline of 12 and be fine. It's only a matter of positioning. And bows are awesome for decreasing enemy's efficiency.
2. Having meat bro is good, but each death decreases morale. It's still better if they survive to max out morale. Just be wary of their starting stats and stars so you can estimate is final strength and see if it suits your strategy.
3. The important thing is how you make all your bros synergize. Your level ups should take into account your global strategy and formations.
4. Take the easiest ambitions to increase your fame and get access to better contracts. Harder ambition are for later.
5. Caravan contracts are great if you want to increase 'chances for named items to spawn in cities with great Smith and armorer. That' s a good alternative to raid camp and champions. They're also safer usually.
6. It works for any kind of goods. Check prices often. The more money you have, the better the gear you'll be able to buy.
7. Learn contracts and know what you can take. Any contract is good if you know how to fulfill it fast.
8. That's where positioning shines. You can take harder foes if you know what formation to use and what target prioritize. The game is not a matter of level and skill value, those are secondary. It's a matter of taking advantage of the environment and trick AI. For example, I don't fight lindwurms because I never developed a good strategy against them. The rest is fine, I can take them whatever the fighting map given to me.
9. Do it with the good retinue that avoid losing reputation and offers more negociation rounds. Because negotiating affects the rep gain with the city you're negotiating with. Nobody likes someone who's too greedy, unless he's convincing enough.

You can ask for more money at least once without any penalties except for a very small reputation hit.

Originally posted by Santo:

You can ask for more money at least once without any penalties except for a very small reputation hit.

There's a small chance that you'll piss off the contract giver after asking for more money a single time. It's pretty rare in my experience but it's still not 100% safe to ask for more money only once

Appreciate the feedback on my thoughts.
So, tried a couple of things outside of my comfort zone

A) Accepting the first bid does seem to get settlements to like you a bit faster.
B) Bows are stupidly inferior to Crossbows. I'd like to hit my foe this week, thank you.
C) Caravan's main stupidity is that they will never avoid trouble, and that trouble can end your run. I suppose if you're maxxed out, what do you have to fear, but I fear a lot in this game.

Caravan are very rarely deadly, you can start that kind of contract early even though your finance won't make it that profitable. After 10 days you should be able to make this contract profitable.
Archer are better than crossbow but it takes time as archer is efficient with high range skill and some specific perks that'll allow to weaken enemies ability to hit you (overwhelm and fearsome). The damage output of your bros isn't necessary important. Some are support: bannerman could have a much better weapon but you'll lose the resolve bonus, an "assassin" can use bombs and nets before using his dagger, the archer decreases hit chances and can decrease morale like a crowd control cleric/mage would do.

On caravans: remember that you *always* have the option to run from the fight. It hurts if you lose income of long trips but you should only accept short caravan missions, because of this but also because you may as well waste 4 days with not a single fight.

I like caravans... if I have a bunch of wounded bros, often there's no fight and the downtime allows to heal or if I'm going to a place anyway and don't plan to make a detour to bust some camps. Generally I find it the least interesting type of contract, like the cargo delivery comparatively allows to take a trip off the road or simply travel faster.

Side note: if the caravan goes through a large portion of road without settlements, you should expect a busy trip.

On bows:
I think they have a niche indeed. Crossbows definately work too. The goblin's crossbow in particular is stupidly good, damaging through heavy armour and the knockback effect allows to waste 2h ennemy turns by knocking them out of swing range.

There's a LOT others can tell you about how to play, and they can all be correct. However, you probably would be better off watching some Youtube guides and play-throughs.

Only one suggestion from me: DON'T go IRONMAN. You may want to run normal difficulty as well.

You need to learn (a lot) from all the terrible mistakes, reflect, and find better alternatives, WITHOUT starting all over again. That's the fastest way to get better at this game. After 2 or 3 good endgame, then we can talk IM.

@ Woodie: All seven campaigns I've played have been relaxed Ironman.

This is part of why I've leaned so far into very calculating strategy for the game, is because busting up bad is basically lose game--so turning down high risk extreme reward jobs is often the play.

Hi @Threeist, good to see you at a different stage with the game. There's a broader question for growth then. For the company to get stronger, my suggestion is: don't get fixated with contract jobs- it's just not very efficient for the bros' time.

For the beginning, sure, everything needs to be calculated and money is a necessity. But it's possible to ramp beyond these contracts quickly. And afterwards every 3s job would be of no more risk, rather a question of: "Do I have time to do it along the way?" or "Does this enemy have higher chance to drop the (top tier/named)gear or material I want?" etc.

The alternative? Raiding is an option, but more common one is exploring the wilderness to clear out the camps. It's far more rewarding in money and gear (riskier also, but you can learn to fight them when not in IM). Try to increase the number of camps cleared during one expedition, until every camp (Sea of Tents included) is set ablaze wherever the company decide to take their little "field trip". A couple of legendary locations can be treated as the final challenges of the game, but others can be tackled mid-game relatively easily to give a quick boost on the weapon/gears.

New bros you recruit in the mid game require micromanagement. But only if they are good, which is defined by stats, stars and traits, not by cost.

Use potions of knowledge, training halls and potentially drill sergeant so they level up quicker.

Vs enemies with no or weak range weapons, give them a reach weapon and if you have them, a mushroom. I like the Goblin Pike for its ability to attack and move twice and hit% bonus. Swordlance/warscythe are awesome Vs wiedergänger.

Vs enemies with good ranged (brigands, nomads, goblins) give them a kite shield, spear and dagger. Surround the last fleeing enemies and have your newbie finish them off for experience.