[sblock=OOC]This lady is up high, right? 3rd or 4th story? I think getting to her through the sky bridge is probably safer than her jumping. We at least need to try a safer option. If things go south, then we jump.[/sblock]
"She's too high up. The sky bridge might be safer and we might have a chance to keep the fire from spreading."
Caleb whispers, "לציית
," and then with his voice booming in a loud echo, he shouts, "Hold on! We're coming!"
He mutters to himself, "הַדְרָכָה
," while touching his forehead as he rushes towards the adjoining building. He shouts, "לציית
," and the door flings open in front of him. He rushes to the skybridge to the roof and runs across looking for a way in.
Cast Thaumaturgy to enhance voice.
Cast Guidance for whatever action I'm going to need in a moment. (Concentration)
Cast Thaumaturgy to open doors in front of me (I'm assuming no one is locking their doors when they rush into the streets during an aerial bombing).
Cast Thaumaturgy whenever I encounter some flames to make them flicker and hopefully give me advantage on whatever skill check I need to get to the woman and get out.
The plan is to go across the skybridge to the roof of the burning building, get her out the same way, and then try to cut the bridge in some way to keep the fire from spreading to other buildings through it (if we get to that point, Thaumaturgy to project my voice to warn people below)
I don't know what skill you would like me to use, so here is a base roll.
WotBS Caleb skill check with guidance: 1D20+1D4 = + = 11
If you'll allow Acrobatics, it's +1. If it's Athletics, it's -1. If you'll give advantage from Thaumaturgy, then here's another roll.
WotBS Caleb skill check if advantage: 1D20 =  = 13
Guidance from the first roll would pop that to 14.
If anyone comes with me, I'll gladly provide support instead.
If any players care to go with me, feel free to narrate the above with you taking the lead and Caleb following behind.[/sblock]