The shroud (the plastic AC cover) originally had only four screw holes. Two in the front and two near the rear on each side. Someone drilled in a couple extra and tried to reinforce the plastic with (I'm guessing) fiberglass tape. Looks like you need a new shroud.
Another issue is that AC unit is setting in a pan, which is an Airstream specific item. That pan is setting on top of big gobs of caulking, probably what you are seeing. That pan on your trailer is 16+ years old, probably cracked and leaking. There is a better way. People are converting the drain pan system to drain cups. Use the forum search to find several threads.
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Alan
2014 Silverado LTZ 1500 Crew Cab 5.3L maximum trailering package
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