Okay I suppose I can see that it feels too hard. This isn't exactly unplanned for though, and it's not unwinnable. The most obvious solution is to just outright turtle.
Well, I wouldn't say 'too hard'. But it is definitely getting complex enough to the point we need to develop a consistent strategy spanning several turns if not years, and stick to it regardless of personal stances on the matter.
Right now we are being wishy-washy, swinging between the extremes and making plans on the spot to suit the momentary needs. We try this thing, get burned, call each other names, abandon the idea and try that thing instead, get burned, then change directions and priorities again, and so it goes.
I am pretty sure that this has become unsustainable. I think Void Stalker was the only player who had made attempts to plan for several turns ahead, or at least the only one who voiced them so we knew what we were getting into when voting for their plans. I'd like for this to become our policy.
And yes, turtling is one alternative I proposed. That, and maybe trying to establish a reserve? Some kind of warrior pool that we could cannibalize to restore our most combat-capable units? My plan would be to train the levi, upgrade them to footmen, use them to patch the holes, buy another levi etc. We may end up with occasionally running out of reserves, but this should last us until the war ends, and then we may be able to call on Kaleb again and join forces.
Alternatively, and I propose this knowing full well it would be one of the dumbest decisions this quest will have ever made, perhaps the dumbest, but if it works we'll be ~50% out of the woods:
A winter offensive
Now, I hate to be the one to shoot that idea down, because I am a man of YOLO myself, but...
We aren't desperate enough for a Hail Mary. In fact, our economy has never been doing better, our defences are nothing to scoff at, and our supply lines are unassailable by the orcs unless we get sieged, which... frankly, puts more strain on them than on us, especially during winters.
A winter offensive is an immensely costly affair... which you already know, or you wouldn't disparage your own idea, but it never hurts to reiterate just how bad it is for an attacker. Not only do they take attrition and morale losses, suffer from the inability to start fires without wizardry, and have a hard time moving through the snow in heavy armor (or in the orcs' case, trying to plow-ride through the snow) while dragging supplies through the thicket, but they will have to face an enemy who didn't have any of these hurdles, in a fortified location. And since most people are sane and stay inside during the winter, I give it good odds that we'll be facing an entire complement of orc troops, because they have nothing better to do but sit on their butts waiting for the snow to melt so they could start raiding. Add to this their numerical superiority, and this starts looking pretty bleak.
These types of diversions work best when there is a soft target the enemy wouldn't think to protect because they'd count on the weather to do it for them, but the orcs have no towns or villages to sack, nothing but the outpost made for the sole reason of hosting troops and armed to the teeth. We'd be attacking the hardpoint at a disadvantage.
I can't in good conscience put everything on a small chance when I am certain we can weather their attacks, even if we have to go through a lot of pain in the process.
Of that Hail Mary... We surely could book a ship to transport us to the nothern border of Overgrowth. It would make it both faster and safer.
Also, since it would basically hinge on Olivia - we probably could take just her and skirmishers to scout for her - we probably should do some more equipment for her, particularly stuff that would allow her to reduce their base into rubble quickly.
That is an interesting idea, but when do we undertake this expedition?
It will also make the orcs prioritize the docks in their next raids. Not that they are terribly safe now, being the only structures outside the paliside...