Tharanau is getting ready for the fight, bolstering his resolve with a good pep talk (casting false life, 7 temp HP - total HP 32).

Then he chimes in with the suggestions.

"I could levitate you up to the top of the tower, Progo, if you think that's a good idea. However, it might take a little while to get you to the top depending how high the tower is (can only levitate upwards 20ft per turn)."

(I hadn't considered the tower hight, Progos needs 80' shooting distance to not have disadvantage, steady aim can counter the disadvantage how tall do we think the tower is?)

Oh my bad, the tower is actually lower (around 20 feet above the ground.) Than the main building (which in its center part is around 40 feet above ground) so approaching from southern-western side would give you some cover.

Quote from Wakharashq >>

Oh my bad, the tower is actually lower (around 20 feet above the ground.) Than the main building (which in its center part is around 40 feet above ground) so approaching from southern-western side would give you some cover.

 (In this case this option would be the safest course, I think. As soon as we are closer we should be able to take out one orc without too much noise and then we would still have the drop on the others.)

Goraseth agrees. Let’s come from the south west

Circling around from the western side you see from the distance there is much more occupants wandering around the courtyard and chilling in the afternoon soon. 

(Does this seem larger then a Orc scavenger group? Perhaps they are a group they could reason with? What do the larger ones look like? Looks like there are different types of creature markers on the board, are any of them half orc?)

You would not be able to discern exactly what they are at a distance far enough to not be seen. 

"Progo thinks we should wait for nightfall, hopefully most of them retreat to the building for nighty night time. We sneak from the southwest, those who can't see led by those who can. Progo silently takes out the guards on roof tops and see who left in the yard to deal with without sounding the alarm. Then assist the exit points of the building and decide whether to wake them and get them stuck in the doorway, or wait till morning to start picking them off as they come out. Hopefully not in full force. If multiple exits, we will have to figure out how to be decide ourselves to cover them, or find ways to block some. If things go wrong plan to run back to where we fought the other ones and make a stand there again. If we like Progo's plan, we should rest now and be ready for evening adventure!"

Yes, attacking in the evening makes much more sense. These are too many enemies to confront head on. 

„Ok, but do we really need to get in there? We could also first check out the ranch. If we must attack, I agree, we should wait for nightfall.“

"We still have surprise on our hands at the moment, once that little scavenger party is discovered, they might put more guards out. Progo does wish we had a bit more information about those inside. There is a lot, and big ones. But talking leaves no room for suprise after. If the group wish, Progo could approach and see if they will talk or not? Again, no surprise option after that. But maybe they could be good allies?"

At this moment (which is about 2-3 hours to sundown, and moon is getting visible at its crescent shape <so no much light of it at night>) 3 of the orcs are going out of the walls trough the northern entrance. They are going in the direction of Conyberry. 

"Looks like a small bunch are heading  out, maybe we catch up with them and see of they are friendly or attack om site which will tell us about the lot as a whole "

"Good idea! Let's follow them."

"Let's hide and attack them, far out of sight from this outpost. It's true, there are too many enemies inside the shrine." Tharanau shakes his head. 
"Let's attack and catch this group, and ask for details. What they're doing here, and how many are inside the shrine." 

(I assume the group would have to make haste to catch up to those that left as we are still 400-500 feet away now to the south west and have to stay that far away while working our way around unseen.)

"Progo thinks it may be worth trying to talk civil with them first. Maybe we can make some arrangements with them that benefit far more then half of us dead. Thise big ones could come in handy fighting a dragon."

"Sure Progo. Let's make haste and catch up with them. I can try talking to them. Would you want to try and forge an alliance with them against the dragon?"

"Progo is at his best today, so many good ideas! They would improve the chances against the dragon greatly! If they feel so inclined, or if you can pull the right strings to make it so," Tryn glances to Tharanau.

Huffing between each breath as the group hussles towards the band of now travelers. "Progo is always at Progos best. Today, yesterday, always Progos best!"