wait , so they want him to spend a month or two to go get the ship but won't pay for expenses or any other fees that might come up?

Even debating if Leo would take it since he has that mentality or paying back what he owes. The longer they wait the more other creatures are going to find that ship, my top pick would be changelings since they have an actual spy network due to their skills.

I'm on the fence with this Twilight, because Non was here to help she and her friends hasn't gone through any hardships to toughen them up or the fact that Leo's voice getting loud was enough to scare her has me wondering about their status as friends unless they don't yell in this equestria.

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The wincing is more because they don't like the yelling vs them not being able to handle it. At this point, they would be in the middle of season 2-ish. So they have been trough a bit, but not alot. Hope that clears it up a bit.

Also, they are paying to get him there, but things like clothes, food and the like are on him. Remember he's practically destitute, so having to buy extra anything is difficult atm.