To be fair, the castle idea was our poor call, 1) the priestess escaped and shouted "Jolly will be back for revenge!" 2) Jolly leaves the castle at midnight and comes back so we know
he can get before 8 hours, what were we thinking when we decided to long rest tsktsk 3) I was going to say something about not letting me have the 3/4th watch because that's when Jolly is most likely going to reach us from wherever he came from, but WIS 8 and carefree attitude heh.
1) We're not taking a long rest
2) As explained in my first post no one has realized that we survived the 'trials', otherwise we'd already be surrounded. The monks were training, no pursuits, no alarms have been raised (of we know)
3) With Leomund's Tiny Hut they can't even open one of the two doors so we only have to be focused on one door.
4) I used Pass Without Trace from the guard room and we arrived at the Training Grounds, even if they hired 100 rangers it's impossible to track us physically. They can only magically track us, which is a possibility.
5) I'm not afraid that we'll be ambushed on the way to the outside, I am certain we'll be ambushed when we're outside. How do you suppose we're going to, first of all, get to the front gates unnoticed with 17 clumsy noncombatants and out of the 6 combatants half of which can't even sneak properly.
- Worse comes to worse the guards are going to be intimidating enough that half the noncombatants will try to hold us down (grapple) so that "they'll be spared"
- Best case scenario the guards threatens to slaughter the noncombatants if we don't lay our arms down. We might lose the cleric (you) and Aran because, well, RP =D
Point is, there is no sneaking out of the monastery. I'd rather take the chance to get the short rest in the training grounds after we clean up the blood spatters outside with prestidigitation. There's only 1 entrance we have to look out for and everyone can be inside the grounds rather than going up facing multiple traps and/or ambushes with our pants down.
Worse case scenario if we take a short rest:
-Short rest is unsuccessful if they bump into the grounds
-If anything they'd be surprise to see us in the training grounds if they randomly wandered in haha..but yeah, most likely just normal initiative. No traps, no ambush, no hostages.
-A fireball is thrown into the room. In which case we probably won't fare any better if we're ambushed when we're out in the opens.
There are literally no scenarios that I can think of that could be less riskier than getting the short rest. I'd be more inclined to get out without a short rest if we do not have hostages, but we have a ton of them...
TLDR: We'd be in a much better shape to be ambushed after the short rest than before.