Assuming Thwip’s command/suggestion to split into two teams is taken: Given the disguise of the courier and the bodyguards I think it’d be wise to make a beeline for the docks to see what sailing options there are. Our customer is waiting for their fancy whatevers after all.
Then maybe we can agree to meet up at the docks. Or the inn if nothing is sailing out that day.
Umm… About that… I have a response to Eoin’s comments. Before he gets us all dressed up.
Add it in, we can retcon things if necessary.
It’s always a balance between waiting for player input vs delaying the game. The occasional minor time-reversal is inevitable.
She’s a smart, proud kid with trust issues. At least she didn’t steal your horse (yet)!
Well, that’s a start 
.
On Eoin’s part, he was getting irritated by what he saw as someone carrying on the squabbling and point scoring while there was a job to do.
And on my part, I thought I was playing him a bit too detached and unfazed by the tension in the group. The way I read Hayu’s tone and her addressing him directly gave me an opportunity to course correct.
Any Better Call Saul fans around? That’s the same scam Jimmy and Marco pull with the Kennedy dollar in the final episode of season one.
“Elliot’s the fiddle.” Parker, finally figuring out the con in “The Studio Job”.
BTW: the trading post is not walled. It’s just an inn (with attached stables), some cattleyards and the docks. The terrain is flat and clear; you’d need to go a fair way to circle the settlement unnoticed.
Is the horse branded in any way? What about the saddle/bridle?
We could just come in together and claim we met on the way should anyone ask. I think the most important bit is that Thwip and Ranar avoid the stables as much as possible, even if they have good disguises.
Ranar’s looking for any noticeable comings or goings at the trading post, indications of unusual activity, and trying to get a feel for the general activity level of the river and trading post.
Or not wait for 'em to ask by parting ways at the entrance with a hearty show of, “Goodbye, nice to have met you, good luck in your travels!”'s as we go our separate ways. 
My vote is for one group to head in, and the next lot waits a plausible amount of time and then follows on. It’s easy enough to have two groups travelling in the same direction, down the same road, without ever meeting up.
But if we’re feeling paranoid enough, Hayu and Eoin can circle around with the horse. At a pinch, they could double up on the horse to move faster if they don’t have a bunch of extra stuff with them.
Whoops, sorry; forgot to answer that one.
The horse is of good quality, and battle-trained. The tack is unmarked, of moderate quality and decently cared for, but has seen hard use.
The horse is branded, with a symbol that isn’t familiar to you. It also has a partially-healed bullet wound on its chest.
A horse like this would cost several thousand dollars to buy; what you can sell it for, and whether it’s worth the risk, is an entirely separate matter.
It is possible to transport a horse on some ships, but it isn’t cheap. Horses are a pain in the arse on a ship; big, fragile, messy, panic-prone and dangerous.
The game’s with you folks; keep chatting, or give me a solid consensus on what everyone is doing so I can move things forwards.
No rush, but let me know when you get there.
Thwip is getting purdied up and ready to enter town with his dwarven posse.
Ranar’s still looking for any noticeable comings or goings at the trading post, indications of unusual activity, and trying to get a feel for the general activity level of the river and trading post.
I’m assuming it’s a pretty quiet, low-traffic place?
Yup. Gets busy on market days, but not today. Just the occasional small group of passengers boarding or leaving passing boats, and a few locals getting meals at the inn.
Well, that puts as at an impasse in terms of moving things forward. Definitely, one of those situations that would be a lot easier to resolve in a real-time game.
I’ve pretty much laid-out my argument for the disguises and procautions in various in-character posts (TL;DR Elven assassins, bloodthirsty guards that may/may not hunt over really long distances, and how to make it harder for them to find us just by asking after that really weird group).
@strokeybeard
So, if Sasha refuses to be disguised, or stealth it, what is he willing to do? Because he’s probably the most distinctive party member being a beardless dwarf with an unusual crossbow. Both of which are pretty much unique to this part of the world as far as I know - he’s basically Varric in a world of standard Tolkien-issue dwarves.
I’m not sure there’s much sneaking to be done. Once we book passage we get on and go. We still have the problem of a distinctive horse and as Sasha said, we were attacked in the wilderness and assumed bandits.