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Strange, I'm 17 hours in the game and had my share of epic 400 vs 400 battles with flanking cavalry, prolonged infantry skirmishes and crossbow volleys. And I think the only thing keeping my army from getting totally destroyed every time is good healer companions in party.

Agreed, in warband sieges were an exceptional way of gaining reputation, especially when you talked to everyone on the feast after a successful siege, it had a certain roleplay feeling to it. But here the only reliable way are not imprisoning lords and doing their quests as far as I know.

Haven't had much trouble with upgrading troops, at first hours of the game, surely, but when you get past it, you'll have most of your army as high tier, which are easily replacable by hiring prisoners, also villages and towns start offering better units for hire later.

Just do it in multiple tries, you can always flee after killing some, even if you die and have units in you army left you will be dragged out and can try another night. Actually this is something I like in bannerlord so far, you can't make assumptions, like "game makes me go into 6 vs 40, so I have to do this in one go", it's not necessarily logical, but it's fun to learn anew.

If you have spare time and don't afraid to lose some troops, you actually can flee after killing a couple of bandits to return the other night(because there is a delay for another attempt after fleeing). Even without this, you can even die there and try again later, as long as you have spare troops outside. Dead bandints won't regenerate.