I don't think it would hurt to fill the battlefield with as many creatures making attack rolls as possible.  If the dragon gets off the ground, it can be surrounded by... I dunno, like 30 Medium creatures.  The number is really high.  But that won't matter unless whatever you summon can fly, too. 

Presuming that the dragon is only large enough to take up a single 5' cube, it can be surrounded by up to 26 flying creatures.  But that figure is highly conditional and dependent on the relative speed and maneuverability of all participants.  Air elementals fly at 100 ft. ( perfect).  That means they will be at a great advantage against anything of equal or lesser speed than them, and probably able to mob their victim.  But their maneuverability will be of little help against something that can move faster than 100 ft. 

Unfortunately, you guys don't know how fast a dragon can fly, so planning based on this will be difficult.  If the dragon is faster, then your best hope is to keep it on the ground in the first place, and if it does get airborne, you'll have to hope that your summoned help will be able to get close enough for long enough to slow it down.  Theoretically, enough elementals might be able to mob a dragon and put it into a situation where it cannot fly fast enough to keep itself airborne. 

If something goes wrong and the dragon can outrun them, then you're going to have a really eventful few days ahead of you. 

The local terrain is ruggedly hilly.  At present, you are in the bottom of a valley.  If you were to go NE, the valley would narrow into the space between two hills.  This would eventually happen to the SW, but the hills are rather less steep, and it would take longer for them to narrow.  Some way to the east, there is another hill.  It is a steep slope, and there's the expected undergrowth and tree cover.  But no cliffs or rubble. 

White squares represent the valley floor.  It's reasonably flat (flat enough not to affect movement or combat).  You can see that there are brown dots.  These are ordinary trees.  I won't hash out their effects; they're climbable and provide the usual cover bonuses, etc.  I'll summarize them in the OOC thread. 

Grey stippling represents boulders and rocks of size significant enough to affect movement.  They are "dense rubble."  It costs 2 squares of movement to enter a square with dense rubble.  The DC of Balance and Tumble checks on dense rubble increases by 5, and the DC of Move Silently checks increases by +2.  As a result of the movement penalty, dense rubble counts as difficult terrain; you can't run or charge through it.  On the bright side, neither can most things that might want to attack you. 

Orange squares are light undergrowth.  It has the usual effects of light undergrowth.  I'll leave a potted summary in the OOC thread, if initiative starts up.  You can see that if you swing a line 120 ft.  from the cave entry, there is no undergrowth.  And in fact, there's very little vegetation of significance in this area.  That's the dead zone that was discussed in the IC thread.  It's unmistakable that SOMETHING has been keeping the area around the cave entry free of plant life.  This makes it very difficult to hide near the cave or sneak inside from the valley floor. 

Area 1 is the simple part of this map. 

As you can see, there also is an extensive section in dark grey.  This represents the hillside.  At all times, you may assume that the hillside represents a "steep slope," on which the downhill side is toward the nearest white square.  Characters moving uphill (to an adjacent square of higher elevation) must spend 2 squares of movement to enter each square of steep slope; as a result, you cannot run or charge uphill.  Characters running or charging downhill (moving to an adjacent square of lower elevation) must succeed on a DC 10 Balance check upon entering the first steep slope square.  Mounted characters make a DC 10 Ride check instead.  Characters who fail this check stumble and must end their movement 1d2×5 feet later.  Characters who fail by 5 or more fall prone in the square where they end their movement.  A steep slope increases the DC of Tumble checks by 2. 

Yellow patches are light undergrowth.  They are in yellow to help make it clear that they're on the hillside. 

The hillside also features trees.  They are not as visible as I would like, but I have done my best. 

The darkest area of the hillside, nearest the SE edge, represents a cliff, roughly 40 feet high.  A cliff typically requires a DC 15 Climb check to scale.  This cliff is not perfectly vertical or perfectly sheer.  Figure that for every 20 feet you ascend, you will automatically move 5 feet into its area.  If you fail your Climb check by 4 or less, you make no progress.  If you fail by 5 or more, you fall from whatever height you have already attained. 

Getting up onto the hillside is possible; there are areas of steep slope to the extreme east and south edges of the map.  You can ride straight up those slopes, albeit at a slower pace than you may want. 

It is not super-evident, but the hillside is translucent because the cavern system that Fanax is about to investigate lies underneath it.  Currently, it is masked off in black so that you can only see the parts of it that are exposed to Fanax's darkvision and/or the intrusion of natural light from outside of the cave. 

As Fanax (and others) move around inside, I will unmask new areas as your vision reveals it to you.  I will shadow areas that are not actually within the view of someone's darkvision or a light source, even after they are discovered. 

Zathrus wants to be further away.  Maybe on the other side of those two trees in the upper right-hand part of the white area.  With his horse hitched to the next tree south. 

I assume that Cha'nek isn't nearby and wouldn't want to come near the cave unless pushed to do so?  Zathrus isn't interested in making the amount of noise that yelling repeatedly at the disobedient wolf would take, and in fact thinks Cha'nek might be the smarter of the two of them in this instance. 

This looks solid to me.  I mean I recognize I volunteered Yonah for this gig but he's probably stronger than any of the goblins and was also carrying the rope in question.  I feel like together, we have the best chance of that part of the "plan" succeeding.  Obviously this is all less than ideal but when Fanax made it clear he was going inside no matter what, I figured why waste the bait?  Especially if he dies, there's no way anyone else is going to volunteer to try again. 

White squares represent the valley floor.  It's reasonably flat (flat enough not to affect movement or combat).  Brown dots represent ordinary trees.  A creature standing in the same square as a tree gains a +2 bonus to Armor Class and a +1 bonus on Reflex saves (these bonuses don’t stack with cover bonuses from other sources).  The presence of a tree doesn’t otherwise affect a creature’s fighting space, because it’s assumed that the creature is using the tree to its advantage when it can.  The trunk of a typical tree has AC 4, hardness 5, and 150 hp.  A DC 15 Climb check is sufficient to climb a tree. 

Grey stippling represents boulders and rocks of size significant enough to affect movement.  They are "dense rubble."  It costs 2 squares of movement to enter a square with dense rubble.  The DC of Balance and Tumble checks on dense rubble increases by 5, and the DC of Move Silently checks increases by +2.  As a result of the movement penalty, dense rubble counts as difficult terrain; you can't run or charge through it. 

Orange squares and yellow squares are light undergrowth.  A space covered with light undergrowth costs 2 squares of movement to move into, and it provides 20% concealment.  Undergrowth increases the DC of Tumble and Move Silently checks by 2 because the leaves and branches get in the way, but the concealment enables Hide checks. 

Dark grey squares represent the hillside.  At all times, you may assume that the hillside represents a "steep slope," on which the downhill side is toward the nearest white square.  Characters moving uphill (to an adjacent square of higher elevation) must spend 2 squares of movement to enter each square of steep slope; as a result, you cannot run or charge uphill.  Characters running or charging downhill (moving to an adjacent square of lower elevation) must succeed on a DC 10 Balance check upon entering the first steep slope square.  Mounted characters make a DC 10 Ride check instead.  Characters who fail this check stumble and must end their movement 1d2×5 feet later.  Characters who fail by 5 or more fall prone in the square where they end their movement.  A steep slope increases the DC of Tumble checks by 2. 

Dots on the hillside are also trees, with mechanical effects identical to those already described. 

The darkest area of the hillside represents a cliff, roughly 40 feet high.  A cliff typically requires a DC 15 Climb check to scale.  This cliff is not perfectly vertical.  For every 20 feet you ascend, you will automatically move 5 feet into its area.  If you fail your Climb check by 4 or less, you make no progress.  If you fail by 5 or more, you fall from whatever height you have already attained. 

The interior of the cavern has natural stone floors.  It takes 2 squares of movement to enter a square with a natural stone floor, and the DC of Balance and Tumble checks increases by 5.  Running and charging are impossible, except along paths.  The walls and ceiling of the cavern are unworked stone.  It takes a DC 15 Climb check to move along an unworked stone wall. 

Obviously, you can ask for clarifications and the like at any time, but if you have questions, this is a particularly good moment to ask them. 

It looks like your new map has replaced your old map in your previous post so I can't go back and check if there's a tree in the same square as Zathrus.  If not, he'd like to be in a square with a tree. 

I have relocated Zathrus to a spot one square directly E from the location shown, to put him in the same space as a tree.  Grimvaalk is in a square with undergrowth, so he has concealment and is capable of using the Hide skill. 

Somewhat vexingly, there is no Handle Animal option to induce an animal to hide or try to move quietly (not even as a trick in its own right), whether you are riding it or not.  I think that this probably is an oversight rather than an intentional gap in the rules, and I don't know if I personally would rather have it be something that animals tend to do on their own, or a trick that you can teach them. 

I guess we probably ought to has that out.  It hasn't mattered much in the past because people have tended to use horses as their mounts, and there's really just no way to make a Large horse or mule stealthy.  But wolves have positive modifiers to Hide and Move Silently, and are predatory animals by nature.  So it may be somewhat important now. 

I feel like if a creature's standard stat block indicates it has ranks in Hide or Move Silently (or a racial modifier to either), that tells us something about how it is naturally inclined to behave.  When stalking prey or exposed to a potentially dangerous situation, maybe wolves would just try to make themselves scarce by default and you would need to tell it to do otherwise (probably by commanding it to perform a trick). 

I also like the idea of a trick just for that purpose - to try to get the animal to hunker down as low to the ground as possible or step more lightly.  It sounds like the kind of thing you could teach an animal to do, even if they don't necessarily know why you want them to do it.  I dunno how popular such a trick would be when they come at a premium, though. 

I like the idea of the animal hiding on its own because its in its nature to do so.  I also like the idea of a trick.  Perhaps two tricks?  Hide for laying low and Stalk for attempting to move while hiding? 

Okay, we'll treat it as a trick. " Pushing" an animal to perform a trick it doesn't know is a DC 25 check using Handle Animal, and it takes a full-round action. 

Supposing that Fanax takes 20 rounds to find (or get found by) any dragon that may be in that cave and either die or get out, you have time to take 20.  I think Grimvaalk is technically capable of succeeding with less than a natural 20.  Gorx isn't, quite.  Zathrus has no hope of success, and Fanax is busy with other stuff. 

I don't guess it matters TOO much, since there's no way in hell that you're going to get all your animals to hide.  And even if you did, Zathrus's horse and Gorx's mule have negative Hide modifiers. 

If you are hidden, I think you'd possibly stand a chance of getting a shot on the dragon without applying its Dex modifier to AC, which might be helpful.  But Zathrus and Gorx may not even be planning to do anything that would require an attack roll, so maybe they don't really care. 

Grimvaalk might get some utility out of hiding, but I guess he should dismount or get his wolf to hide if he's going to do that.  It doesn't make a lot of sense to try to hide while you're straddling a creature that isn't hiding at all. 

That would have been very helpful for him, yes.  He should get right on it, in case he lives through the next few minutes. 

You might want to think about it a little more; his wolf is currently trained as a war mount, so it knows the "attack" trick.  But the base trick only makes it willing to attack humanoids, monstrous humanoids, giants, and other animals.  If you want to make the mount willing to attack ALL creatures, that counts as two tricks. 

@Board Rider, you can proceed.  Per the map, Fanax's darkvision is of sufficient extent to show him that the cavern looks like it branches.  There's a right/north branch, and a left/south branch. 

If he's trying to be stealthy, then he'll need to move slowly and try to stay near sources of cover.  Move Silently checks take no penalty if he moves at half speed or slower (so 15 ft.  as a move action, or 30 ft.  as a full round).  If he moves faster than that but slower than his full speed of 30 ft.  move action/60 ft.  full round, he incurs a -5 penalty to his check.  Faster than that, and it jumps to -20 or so. 

Since the cave floor is unworked stone, he'll actually be going even slower; movement costs are doubled.  So effectively, if he wants to move with no penalty to Move Silently checks, he'll be covering about 1 to 3 squares per round.