Thank you guys for all your inputs.

I just want to make it clear that I would definitely pay Diego for whatever job he's done to my roof up to this point. I am not going to hold him to that $1 in the contract.

I think the $1 thingy is such a glaring issue that it overshadows two of my original questions:

1. Are there other holes in the contract that would give me an out? The $1 is certainly one, but in this case, the more, the merrier, I guess.

2. Since the contract hinges on my insurance claim, would the contract be voided if I withdraw my claim, say, when the adjuster says the cost of repair is lower than my deductible?

Once again, thanks all for your past and future inputs.