1. I hire 12 people as soon as possible, cheap ones. My talented guys I put in the backline and give them a pitchfork or better, if I find a decent polearm early. Check the military settlements with Blast Furnaces / Ore Smelters for cheap armor/weapons from the regular market. Sometimes you will find a 40% repaired billhook for 700 crowns. A good polearm like that will carry you throught he early game.
Fight roaming troops for loot and XP. It is much easier to fight 7 thugs + 2-3 raiders than just raiders. Avoid brigand marksmen/fight them only during the night.
Put your new recruits in the backline with a polearm until they get enough melee defense to go in the frontlines. Also give them heavy armor, if you can. Fallen Hero armor is pretty great for the start, even if it drops them down to 40 fatigue or so, with a polearm he will hardly ever get tired and because of the heavy armor he will also survive marksmen.
2. I stop doing delivery quests at around day 30 because mercs will show up to take my stuff. Early I think the best contracts are tracking down thieves, clear a cemetary. Obtain some relic from plains – forests, snow etc can be hard because you can’t always retreat against skeletons since they have pathfinder and you might not. Usually skeleton contracts are not that hard until necrosavants or legionaires show up.
You can ofc also take on brigand encampments but they are usually more difficult than roaming parties, early spawned camps and thieves contracts.
Try to explore the world a bit and take easy encampments for extra loot and gear. Dagger armored wiedergangers for their armor.
3. This is a tricky one. There are many ways to go about this, but most important is probably to have 12 men. Take marksmen at night.
I would take 6-7 frontliners with shields and 5-6 backliners with ranged weapons or polearms or both.
Prioritize targets. Focus raiders without shield first, especially hard hitting weapons like 2-handers and double gripped military pick, axe, flail.
Usually you want to shoot them before they come close, otherwise engage and stun them, burst them with polearms etc. If you are in a 1v2 or more engagement, use shieldwall!
Try and use the morale mechanics and surround bonuses to your advantage – raiders become much easier if there are thugs with them you can kill fast and trigger morale checks on the raiders.
4. Rus Baer answered that. I think it is mostly affected by the days passed and less by your roster. You should definitely try to get 12 guys as soon as possible and keep buying cheap recruits until you get talented brothers.
5. Take Marksmen at night. If it’s a cemetary contract and you don’t know the exact composition, take the fight at night (if you fight brigands).
Get a falcon (hawk?) for one of your companions to scout out the enemy composition. If you see necrosavants/geists/necromancers you can react or retreat.
Orcs and Goblins are dangerous and should be avoided until you know you can beat them. Never take a fresh recruit against goblins as they will very likely kill him with arrows.