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The good thing about DIY renovations is that lessons will be learned when anything goes wrong.

Alternatively, in my experience, you could hire a tradesman - 95% of them will charge you a premium and then cut every corner to maximize their profit while minimizing their time and effort, leading to the job needing to be redone within a few years. That tradesman knows it's not worth your time or money to risk taking them to court or they will have bankrupted their business to flee all responsibility.

TL;DR: Providing you allow time to research a first-time project properly (and providing it doesn't involve electricity), you're almost always far better off in every way to DIY.

Presumably it is caulked and the sag will handle the rest.

It does look like shit, I will give you that much, but it isn't as bad as you think it is

So? Everyone's got to start somewhere. I think it looks great. If it has some issues, he'll fix them. It'll be a learning experience.

Obsessing over doing everything perfectly the first time is a surefire way to never accomplish anything.

The wires actually go up the vinyl siding a ways before it enters the 2nd floor of this root cellar. Either way, that stuff predates me. Have not gotten around to replacing it yet...